image imagewidth (px) 781 2.34k | question stringlengths 24 302 | choices listlengths 4 4 | answer int32 0 3 | meta_info dict | question_type stringclasses 6
values |
|---|---|---|---|---|---|
Please write the overall reaction equation for this reaction, including the main reactants, products, and key reaction conditions. | [
"Ar–CHO + BrCH₂–C≡CH under dual catalysis of Cp₂TiCl₂ (5 mol%) and 3DPAlFIPN (10 mol%), with Hantzsch ester (2 eq) assistance, in THF solvent, blue light irradiation, at room temperature for 48 h, to give Ar–CH(OH)–CH₂–C≡CH.",
"Ar–CHO + BrCH₂–C≡CH under dual catalysis of Cp₂TiCl₂ (10 mol%) and 3DPAlFIPN (5 mol%),... | 3 | {
"title": "Photoredox Propargylation of Aldehydes Catalytic in Titanium",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00521",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00521"
} | 0 | |
What is the SMILES of substrate 2a? | [
"C#CCBr",
"CC#CBr",
"C#CCCl",
"BrC#CC"
] | 0 | {
"title": "Photoredox Propargylation of Aldehydes Catalytic in Titanium",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00521",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00521"
} | 5 | |
What is the reducing agent of this reaction system? | [
"The reducing agent of the reaction system is Hantzsch ester (Hantzsch ester)",
"The reducing agent of the reaction system is [Cp2TiCl2] (titanocene dichloride)",
"The reducing agent of the reaction system is propargyl bromide (propargyl bromide)",
"The reducing agent of the reaction system is 3DPAFIPN (3,4,5... | 0 | {
"title": "Photoredox Propargylation of Aldehydes Catalytic in Titanium",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00521",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00521"
} | 1 | |
What is the title of the reaction shown in this figure? | [
"Dual Photoredox Alkynylation of Aromatic Aldehydes",
"Photoredox Propargylation of Aliphatic Aldehydes",
"Dual Photoredox Propargylation of Aromatic Aldehydes",
"Dual Photoredox Propargylation of Aromatic Ketones"
] | 2 | {
"title": "Photoredox Propargylation of Aldehydes Catalytic in Titanium",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00521",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00521"
} | 0 | |
What substituents are present on the benzene ring of the products with the highest and lowest reaction yields? | [
"The product with the highest reaction yield is 3d (78%), which has a para F substituent; the product with the lowest reaction yield is 3i (50%), which has a para tBu substituent",
"The product with the highest reaction yield is 3b (86%), which has a para Cl substituent; the product with the lowest reaction yield... | 1 | {
"title": "Photoredox Propargylation of Aldehydes Catalytic in Titanium",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00521",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00521"
} | 0 | |
Describe the reaction conditions for step b. | [
"Substrate 2g with 1 equivalent of 4-methoxyphenyl diazonium tetrafluoroborate, catalyzed by 1 mol% [Ru(bpy)Cl2], in acetone (concentration 0.01 M), under blue LED irradiation, carried out as a flow reaction at a flow rate of 3 mL per hour. Yield 75%.",
"Substrate 2g with 1 equivalent of 4-methoxyphenyl diazonium... | 3 | {
"title": "Into the Blue: Ketene Multicomponent Reactions under Visible Light",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00278",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00278"
} | 0 | |
In reaction step a, which trifluoromethylation reagent is required to convert substrate 2f to product 3? | [
"Use Umemoto II trifluoromethylation reagent (2 equivalents).",
"Use Umemoto I trifluoromethylation reagent (2 equivalents).",
"Use Togni I trifluoromethylation reagent (2 equivalents).",
"Use Togni II trifluoromethylation reagent (2 equivalents)."
] | 0 | {
"title": "Into the Blue: Ketene Multicomponent Reactions under Visible Light",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00278",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00278"
} | 1 | |
In the reaction from substrate 2g to product 4 in step b, what change occurs to the core structure of the compound? | [
"The silyl enol ether structure of substrate 2g is converted into the ketone structure in product 4, and an acetone moiety (from the solvent) is added at the α-position of this ketone.",
"The silyl enol ether of substrate 2g is retained as the silyl ether structure in product 4, and a methyl group (from the solve... | 0 | {
"title": "Into the Blue: Ketene Multicomponent Reactions under Visible Light",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00278",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00278"
} | 2 | |
What is the flow rate in step a? | [
"3 mL/h",
"2.5 mL/h",
"1.0 mL/h",
"1.5 mL/h"
] | 3 | {
"title": "Into the Blue: Ketene Multicomponent Reactions under Visible Light",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00278",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00278"
} | 0 | |
What is the overall title of this chemical reaction diagram? | [
"Coupling SK-3CR with Other UV-Light-Mediated Processes",
"Coupling SK-3CR with Other Visible-Light-Driven Processes",
"Coupling SK-3CR with Other Photoredox-Mediated Processes",
"Coupling SK-3CR with Other Visible-Light-Mediated Processes"
] | 3 | {
"title": "Into the Blue: Ketene Multicomponent Reactions under Visible Light",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00278",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00278"
} | 0 | |
From the data in entries 6–9 of the table, how does reaction concentration affect yield? Why does the yield decrease when the concentration is reduced from 0.5 M to 0.3 M? | [
"Entry 7 has the highest yield (96%) at 0.5 M, while entry 9 at 0.3 M drops to 69%. A moderate concentration (0.5 M) ensures a sufficient effective collision frequency between the activated intermediate and the amine; being too dilute (0.3 M) reduces reactant concentration, lengthens reaction time, and may increase... | 0 | {
"title": "A 1-Pot Synthesis of the SARS-CoV-2 Mpro Inhibitor Nirmatrelvir, the Key Ingredient in Paxlovid",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.2c03683",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c03683"
} | 3 | |
In Table 1, which three coupling reagents were screened in total? Which one is the most effective? | [
"The three coupling reagents screened in the table are: ECF, NMM, T3P, among which T3P is the most effective.",
"The three coupling reagents screened in the table are: ECF, 2-EHCF, T3P, among which 2-EHCF is the most effective.",
"The three coupling reagents screened in the table are: ECF, 2-EHCF, T3P, among wh... | 2 | {
"title": "A 1-Pot Synthesis of the SARS-CoV-2 Mpro Inhibitor Nirmatrelvir, the Key Ingredient in Paxlovid",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.2c03683",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c03683"
} | 0 | |
Regarding the coupling yields of different solvents in the ECF/NMM system, which of the following statements is correct? | [
"THF (45%) exhibits the highest coupling efficiency.",
"2-MeTHF (45%) exhibits the highest coupling efficiency.",
"2-MeTHF (60%) exhibits the highest coupling efficiency.",
"EtOAc (40%) exhibits the highest coupling efficiency."
] | 2 | {
"title": "A 1-Pot Synthesis of the SARS-CoV-2 Mpro Inhibitor Nirmatrelvir, the Key Ingredient in Paxlovid",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.2c03683",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c03683"
} | 3 | |
What is the overall reaction process shown in the figure? Please briefly describe the reaction conditions and transformation relationships for each step. | [
"The reaction first, at 0–10 °C, reacts the carboxylic acid substrate with an activating agent (such as ECF, 2‑EHCF, or T3P) and base (NMM or DIPEA) in the specified solvent for 2 h to generate an activated ester or acyl‑phosphonium intermediate; then the temperature is lowered to 0 °C and the reaction is continued... | 3 | {
"title": "A 1-Pot Synthesis of the SARS-CoV-2 Mpro Inhibitor Nirmatrelvir, the Key Ingredient in Paxlovid",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.2c03683",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c03683"
} | 4 | |
Which yields higher, the T3P/DIPEA system or the ECF/NMM system? | [
"By analyzing the data in the table, it can be seen that the yields of the ECF/NMM system (entry 1-3) are all higher than those of the T3P/DIPEA system (entry 5-9).",
"By analyzing the data in the table, it can be seen that the yield of the 2-EHCF/NMM system (entry 4) is higher than that of the T3P/DIPEA system (... | 3 | {
"title": "A 1-Pot Synthesis of the SARS-CoV-2 Mpro Inhibitor Nirmatrelvir, the Key Ingredient in Paxlovid",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.2c03683",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c03683"
} | 3 | |
How is the Extended SMILES (E-SMILES) of enolic pyrazolone 2a written? | [
"CC1=NN(*)C(=O)C1=C(C)C<sep><r>0:Ph</r>",
"CC1=NN(*)C(=O)C1=C(C)C<sep><a>4:Ph</a>",
"CC1=NN(*)C(=O)C1=C(C)C<sep><a>4:Bn</a>",
"CC1=NN(*)C(=O)C1=C(C)C<sep><a>3:Ph</a>"
] | 1 | {
"title": "Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.1c02571",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c02571"
} | 5 | |
How many different 1a substrates were screened in the reaction? | [
"11",
"12",
"14",
"10"
] | 1 | {
"title": "Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.1c02571",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c02571"
} | 0 | |
Please describe the overall transformation of the reaction, including the substrates, catalyst, conditions, and the type of product. | [
"The substrates are isatin-derived imines (1a–l) and an enol-type pyrazolone (2a); in CH2Cl2 solvent, at room temperature, under N2 atmosphere, 5 mol% of chiral organocatalyst IV catalyzes a 4+2 addition to give chiral 2,3-dihydroindole-3-one products (3aa–3la), affording high yields (30–83%) and enantiomeric exces... | 3 | {
"title": "Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.1c02571",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c02571"
} | 2 | |
What is the pattern of how different isatin imine substrates (taking variations in R1 and R2 substituents as examples) affect reaction yield and enantiomeric excess? | [
"Regardless of what substituent R1 bears (electron-withdrawing or electron-donating), as long as R2 is hydrogen, yields can reach 65–76% and ee is also 92–96%; whereas when R2 is benzyl or methoxy, yields drop sharply to 30–52%.",
"When R1 bears electron-withdrawing groups (such as Cl, Br, F) and R2 is methoxy, t... | 2 | {
"title": "Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.1c02571",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c02571"
} | 3 | |
What is the title or subject of this reaction scheme? | [
"The scheme is titled \"Substrate scope of the catalytic asymmetric enantioselective vinylogous addition (Vinylogous Addition) reaction, focusing on the efficient construction of chiral center-containing trihydroindolone framework.\"",
"The scheme is titled \"Substrate scope of the catalytic asymmetric enantiosel... | 3 | {
"title": "Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.1c02571",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c02571"
} | 0 | |
How many products in the figure contain fluorine? | [
"1",
"2",
"0",
"4"
] | 1 | {
"title": "Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines",
"journal": "JACS AU",
"doi": "10.1021/jacsau.1c00176",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00176"
} | 0 | |
How many types of R2 are there in the substrate? | [
"3",
"4",
"2",
"1"
] | 0 | {
"title": "Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines",
"journal": "JACS AU",
"doi": "10.1021/jacsau.1c00176",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00176"
} | 0 | |
What are the key functional group features of substrate 1? | [
"Substrate 1 is an alkynyl hydrazone containing a terminal alkyne and an adjacent hydrazone (N–N) functional group.",
"Substrate 1 is an alkenyl hydrazone containing an alkene and an adjacent hydrazone (N–N) functional group.",
"Substrate 1 is an alkenyl oxime containing a terminal alkene and an adjacent oxime ... | 1 | {
"title": "Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines",
"journal": "JACS AU",
"doi": "10.1021/jacsau.1c00176",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00176"
} | 0 | |
What is the reaction title of the illustrated scheme? | [
"Mn-Catalyzed Cycloaddition (Manganese-catalyzed cycloaddition reaction)",
"Fe-Catalyzed Cyclizations (Iron-catalyzed cyclization reactions)",
"Mn-Catalyzed Cyclizations (Manganese-catalyzed cyclization reactions)",
"Mn-Catalyzed Oxidative Cyclizations (Manganese-catalyzed oxidative cyclization reactions)"
] | 2 | {
"title": "Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines",
"journal": "JACS AU",
"doi": "10.1021/jacsau.1c00176",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00176"
} | 0 | |
What reaction conditions were used in this reaction, including catalyst, oxidant, solvent and temperature? | [
"Catalyst is Mn(dpm)3 (tris(dipivaloylmethanato)manganese(III)); oxidant is air (1 atm O2); solvent is isopropanol (iPrOH, 0.1 M); reaction temperature 55 ℃, reaction time 2 hours.",
"Catalyst is Mn(acac)3 (manganese(III) acetylacetonate); oxidant is air (1 atm O2); solvent is isopropanol (iPrOH, 0.1 M); reaction... | 0 | {
"title": "Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines",
"journal": "JACS AU",
"doi": "10.1021/jacsau.1c00176",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.1c00176"
} | 0 | |
If tert-butyl hydroperoxide is removed and the reaction is carried out in air, how does the yield change? | [
"According to entry 7, the reaction yield is 82%, observed after adding 10 mol% catalyst and 4 equivalents of PhSiH3 in air.",
"According to entry 6, the reaction yield decreases to 56% and requires 48 hours.",
"According to entry 5, the yield is 84%, indicating the yield did not change significantly.",
"Acco... | 1 | {
"title": "Cobalt-Catalyzed Cyclization of Unsaturated N-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction",
"journal": "JACS AU",
"doi": "10.1021/jacsau.2c00186",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.2c00186"
} | 0 | |
Please describe in words the overall transformation process of this chemical reaction, including the structural change features of reactant 3a and product 4a. | [
"The reaction uses an N-p-toluenesulfonyl-protected terminal enamide (3a) as the substrate; after catalytic radical cyclization, the internal carbon of the alkene and the carbonyl oxygen form a five-membered ring, producing the oxygen–nitrogen heterocyclic product 4a containing a C=N-Ts group.",
"The reaction use... | 0 | {
"title": "Cobalt-Catalyzed Cyclization of Unsaturated N-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction",
"journal": "JACS AU",
"doi": "10.1021/jacsau.2c00186",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.2c00186"
} | 2 | |
Regarding the main conditions of this reaction, which of the following is correct? | [
"In toluene (PhMe) solvent, 2 mol% catalyst 1, 4.0 equivalents t-BuOOH as oxidant, 2.2 equivalents PhSiH₃ as reductant, reaction at room temperature for 1 hour.",
"In toluene (PhMe) solvent, 2 mol% CoII(salen-tBu,tBu) catalyst, 2.2 equivalents t-BuOOH as oxidant, 2.2 equivalents PhSiH₃ as reductant, reaction at r... | 2 | {
"title": "Cobalt-Catalyzed Cyclization of Unsaturated N-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction",
"journal": "JACS AU",
"doi": "10.1021/jacsau.2c00186",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.2c00186"
} | 0 | |
What is the reducing agent of the reaction? | [
"PhSiH₃ as the reducing agent",
"PhMe as the reducing agent",
"t-BuOOH as the reducing agent",
"CoII(salen-tBu,tBu) as the reducing agent"
] | 0 | {
"title": "Cobalt-Catalyzed Cyclization of Unsaturated N-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction",
"journal": "JACS AU",
"doi": "10.1021/jacsau.2c00186",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.2c00186"
} | 1 | |
Write the Extended-SMILES representation of product 4a. | [
"*N=C1CC[C@@H](*)O1<sep><a>0:Ts</a><a>6:Me</a>",
"*N=C1CC[C@H](*)O1<sep><a>0:Ts</a><a>6:Me</a>",
"*N=C1CC[C@H](*)O1<sep><a>1:Ts</a><a>6:Me</a>",
"*N=C1CC[C@H](*)O1<sep><a>0:Ts</a><a>5:Me</a>"
] | 1 | {
"title": "Cobalt-Catalyzed Cyclization of Unsaturated N-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction",
"journal": "JACS AU",
"doi": "10.1021/jacsau.2c00186",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.2c00186"
} | 5 | |
How many steps can this synthetic route be generally divided into? Please briefly describe the type of reaction and the main conditions of each step. | [
"The route can be divided into two steps: the first step is cyclization of substrate 2 with substrate 3 under BCl3/p-xylene (110 °C, 45 min), followed by addition of p-tert-butylphenol and heating in toluene for 2 h to construct the boron-containing SubPz core; the second step is to react the obtained SubPz derivat... | 0 | {
"title": "A Green-to-Near-Infrared Photoswitch Based on a Blended Subporphyrazine-Dithienylethene System",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c04320",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04320"
} | 4 | |
The number of methyl groups in the final product is | [
"4",
"7",
"2",
"6"
] | 3 | {
"title": "A Green-to-Near-Infrared Photoswitch Based on a Blended Subporphyrazine-Dithienylethene System",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c04320",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04320"
} | 0 | |
What is the E-SMILES of 3? | [
"CCCC(C#N)=C(C#N)CCC<sep>",
"C(C#N)(SCc1ccc([N+](=O)[O-])cc1)=C(C#N)SCc1ccc([N+](=O)[O-])cc1<sep>",
"C(C#N)(SCc1ccc([N+](=O)[O-])cc1)=C(C#N)SCc1cccc([N+](=O)[O-])c1<sep>",
"C(C#O)(SCc1ccc([N+](=O)[O-])cc1)=C(C#N)SCc1ccc([N+](=O)[O-])cc1<sep>"
] | 1 | {
"title": "A Green-to-Near-Infrared Photoswitch Based on a Blended Subporphyrazine-Dithienylethene System",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c04320",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04320"
} | 5 | |
What is the title of the reaction shown in this figure? | [
"Suzuki coupling reaction of 5-thiopyrrole boronic ester with A2B4",
"Synthesis of A2B4-type porphyrin derivatives",
"Suzuki coupling synthesis of SubPz–DTE photoswitch 1",
"Synthesis of SubPz–DTE photoswitch 1"
] | 3 | {
"title": "A Green-to-Near-Infrared Photoswitch Based on a Blended Subporphyrazine-Dithienylethene System",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c04320",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04320"
} | 0 | |
Write the Extended SMILES (E-SMILES) expression for substrate 2 (the upper-left molecule in the box). | [
"CCC/C(C#N)=C(/C#N)CCC<sep>",
"CCC\\\\C(C#N)=C(/C#N)CCC<sep>",
"CCC/C(C#N)=C(C#N)/CCC<sep>",
"CCC/C(C#N)-C(/C#N)CCC<sep>"
] | 0 | {
"title": "A Green-to-Near-Infrared Photoswitch Based on a Blended Subporphyrazine-Dithienylethene System",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c04320",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04320"
} | 5 | |
In Scheme 1, why are diisopropylcarbodiimide (DIC) and DMAP used when converting intermediate 3 to 4? | [
"DIC mainly acts as a dehydrating agent in the reaction, dehydrating the carboxylic acid and the alcohol to form a lactone; DMAP acts as a proton-transfer agent, helping proton transfer to accelerate the reaction while preventing overactivation.",
"DIC can form a reactive isourea complex with the alcohol group, p... | 3 | {
"title": "Systematic Route to Construct the 5-5-6 Tricyclic Core of Furanobutenolide-Derived Cembranoids and Norcembranoids",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c01820",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c01820"
} | 1 | |
Please briefly describe the overall synthetic goal of Scheme 1. | [
"The aim of this scheme is to synthesize the key intermediate 4 and accomplish the heat-promoted cyclization.",
"The aim of this scheme is to construct the natural product Havellockate (7).",
"The aim of this scheme is to obtain the Diels–Alder product 5.",
"The aim of this scheme is to construct intermediate... | 1 | {
"title": "Systematic Route to Construct the 5-5-6 Tricyclic Core of Furanobutenolide-Derived Cembranoids and Norcembranoids",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c01820",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c01820"
} | 4 | |
What is the Extended-SMILES (E-SMILES) of intermediate 3? | [
"O(C(=O)C[C@@H](C(C)=C)[C@@H]1C=C2[C@@]3([H])[C@@](OC2=O)([H])C[C@@](O)(C)C3=C1)C(C)(C)C<sep>",
"O(C(=O)C[C@@H](/C=C/C1=C[C@@H](OC(=O)C#C)C[C@@]1(C)O)C(C)=C)C(C)(C)C<sep>",
"O(C(=O)C[C@@H](/C=C/C1=C[C@@H](O)C[C@@]1(C)O)C(=C)C)C(C)(C)C<sep>",
"O(C(=O)C[C@H](C(C)=C)C1=C[C@@H]2C(=O)O[C@H]3C[C@@](C)(O)[C@@H](C1=O... | 2 | {
"title": "Systematic Route to Construct the 5-5-6 Tricyclic Core of Furanobutenolide-Derived Cembranoids and Norcembranoids",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c01820",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c01820"
} | 5 | |
What type of cyclization reaction converts intermediate 4 to 5 upon heating to 110 °C? Why can a stereochemical selectivity of >20:1 be obtained? | [
"This cyclization is a typical intramolecular electrocyclization reaction. Because of the configurational restriction of the chiral carbon attached to the alkynyl ester, the major product's stereochemical selectivity exceeds 20:1.",
"This cyclization is a typical intramolecular Diels–Alder (IMDA) reaction, in whi... | 1 | {
"title": "Systematic Route to Construct the 5-5-6 Tricyclic Core of Furanobutenolide-Derived Cembranoids and Norcembranoids",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c01820",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c01820"
} | 2 | |
Which reagents and conditions were used in the first-step reaction of Scheme 1? What roles did they play, respectively? | [
"KHMDS (THF, –78 → 23 °C) was added first to deprotonate compound 2 to generate a carbanion, which reacted with 1 in a Julia reaction to form a cis double bond; subsequently TBAF (THF, 68 °C) was added to remove the TBS protecting group, yielding the dihydroxy product 3.",
"KHMDS (THF, –78 → 23 °C) was added firs... | 2 | {
"title": "Systematic Route to Construct the 5-5-6 Tricyclic Core of Furanobutenolide-Derived Cembranoids and Norcembranoids",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c01820",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c01820"
} | 1 | |
Comparing the three routes in the figure, in terms of number of steps and atom economy, which route is the most efficient? | [
"b",
"Cannot be determined from the information in the figure",
"c",
"a"
] | 0 | {
"title": "Highly Stereo- and Enantioselective Syntheses of δ-Alkyl-Substituted (Z)-Homoallylic Alcohols",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c04401",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04401"
} | 3 | |
How is the Extended-SMILES (E-SMILES) of the chiral intermediate D in scheme (b) represented? | [
"*C#CC[C@H](*)O<sep><a>0:R'</a><a>5:R</a>",
"*[C@H](*)CC([H])=O<sep><a>0:R</a><a>2:OPG</a>",
"C(C)(C)[C@H]1CC[C@H](C)CC1=O<sep>",
"*/C=C\\C[C@H](*)O<sep><a>0:R[7]</a><a>5:R</a>"
] | 0 | {
"title": "Highly Stereo- and Enantioselective Syntheses of δ-Alkyl-Substituted (Z)-Homoallylic Alcohols",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c04401",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04401"
} | 5 | |
In scheme (a), what are the specific reaction steps from starting material A to intermediate B and then to final product 2? | [
"Step 1: Protect the hydroxyl group on homoallylic alcohol A (to give OPG); Step 2: subject the resulting alcohol-protected compound to mild oxidation (e.g., PCC or Swern) to afford aldehyde B; Step 3: carry out a Z-selective olefin metathesis to form the (Z)-homoallylic alcohol 2.",
"Step 1: Protect the hydroxyl... | 2 | {
"title": "Highly Stereo- and Enantioselective Syntheses of δ-Alkyl-Substituted (Z)-Homoallylic Alcohols",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c04401",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04401"
} | 4 | |
Please, based on Scheme 1, give an overall description of the three synthetic route strategies for (Z)-homoallylic alcohols and their key reaction types. | [
"Scheme 1 shows three strategies for synthesizing (Z)-homoallylic alcohols: (a) from homoallylic alcohol A, protect → oxidize to give aldehyde B, then perform a Z-selective Wittig olefination to obtain product 2; (b) use a metal allenylation reagent C to carry out asymmetric allenylation of the aldehyde, generating... | 3 | {
"title": "Highly Stereo- and Enantioselective Syntheses of δ-Alkyl-Substituted (Z)-Homoallylic Alcohols",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c04401",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04401"
} | 4 | |
Which route(s) use organometallic reagents? | [
"b and c",
"a, b, c",
"only c",
"only b"
] | 0 | {
"title": "Highly Stereo- and Enantioselective Syntheses of δ-Alkyl-Substituted (Z)-Homoallylic Alcohols",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c04401",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04401"
} | 1 | |
How many routes for synthesizing 1,3-butadienyl-2-hydroxymethyl compounds are shown in this Scheme in total? | [
"A total of four different synthetic routes are shown, respectively based on the Horner–Wadsworth–Emmons method, NHC-catalyzed coupling-elimination, alkene–alkyne cross metathesis, and the bromo-acetate NHK method.",
"A total of five different synthetic routes are shown, respectively based on the Horner–Wadsworth... | 1 | {
"title": "Stereo- and Enantioselective Syntheses of (Z)-1,3-Butadienyl-2-carbinols via Brønsted Acid Catalysis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c04663",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04663"
} | 0 | |
In the author's newly proposed reaction between allenyl boronate and an aldehyde, the hydroxyl group of the product originates from which substrate? | [
"From the R group",
"From the allenyl boronate",
"From the boronic ester substrate",
"From the aldehyde"
] | 3 | {
"title": "Stereo- and Enantioselective Syntheses of (Z)-1,3-Butadienyl-2-carbinols via Brønsted Acid Catalysis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c04663",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04663"
} | 2 | |
In the first route, what type of reaction intermediate is reagent A? What is the key reaction type of the intermediate B formed when A reacts with R'CHO? | [
"A is a Peterson reagent (silylcarbanion intermediate); the key reaction for A reacting with R'CHO to generate B is the isomerization of the Peterson hydroxy-silane intermediate.",
"A is a typical Wittig reagent (phosphonium ylide); the key reaction for A reacting with R'CHO to generate B is the Wittig base-media... | 3 | {
"title": "Stereo- and Enantioselective Syntheses of (Z)-1,3-Butadienyl-2-carbinols via Brønsted Acid Catalysis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c04663",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04663"
} | 1 | |
In the third route, F is treated with what kind of catalyst to generate intermediate G? What is the common name of this reaction? | [
"F undergoes a ring-closing metathesis reaction in the presence of a Grubbs II-type ruthenium catalyst, producing intermediate G containing a 1,3-butadiene framework.",
"F undergoes a cross-metathesis reaction in the presence of a Grubbs II-type ruthenium catalyst, producing intermediate G containing a 1,3-butadi... | 1 | {
"title": "Stereo- and Enantioselective Syntheses of (Z)-1,3-Butadienyl-2-carbinols via Brønsted Acid Catalysis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c04663",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04663"
} | 1 | |
Why does the Horner–Wadsworth–Emmons method (A→B→C) usually achieve better (E)-alkene selectivity? Compared with the traditional Wittig reaction, how is its E/Z ratio improved? | [
"The E/Z ratio of the Horner–Wadsworth–Emmons method is mainly controlled by solvent effects and coordination of metal ligands; using highly polar solvents can obtain higher E-selectivity; the traditional Wittig reaction is hardly affected by these factors and usually gives a higher proportion of Z-alkenes.",
"In... | 3 | {
"title": "Stereo- and Enantioselective Syntheses of (Z)-1,3-Butadienyl-2-carbinols via Brønsted Acid Catalysis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c04663",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c04663"
} | 3 | |
From the experimental rate constants (log k) in Table 1, how do the reaction activation energy and rate of dipoles bearing an electron-withdrawing CO₂Me substituent (such as R12–R15) compare with unsubstituted alkenes (such as R9, R10) in their reactions with phenyl azide? | [
"The alkenyl dipoles bearing CO₂Me have no significant effect on the reaction rate; the experimental log k (≈1.4–1.6) is basically the same as R9 (1.38) and R10 (1.18), indicating that the electron-withdrawing group neither promotes nor inhibits the reaction.",
"The alkenyl dipoles bearing CO₂Me, due to the elect... | 1 | {
"title": "Computational Exploration of Ambiphilic Reactivity of Azides and Sustmann's Paradigmatic Parabola",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00239",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00239"
} | 3 | |
Please briefly describe the general formula of the reaction and the structural features of the product. | [
"The reactants are phenyl azide (Ph–N₃) and variously substituted olefinic or acetylenic dipoles (R₁–R₄ varying); under metal-free conditions they undergo 1,3-dipolar cycloaddition to give a five-membered ring product containing a Ph–N–N–N three-atom chain and two new carbon–nitrogen bonds. This five-membered ring ... | 0 | {
"title": "Computational Exploration of Ambiphilic Reactivity of Azides and Sustmann's Paradigmatic Parabola",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00239",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00239"
} | 2 | |
The footnote mentions which two solvents were used in the experimental study? How were they chosen for reactions of different dipoles? | [
"The experiments mainly used carbon tetrachloride (CCl4) and benzene as reaction solvents. For all dipoles, the cycloadditions were carried out in CCl4, and benzene was not needed.",
"The experiments mainly used carbon tetrachloride (CCl4) and toluene as reaction solvents. For the dipoles labeled with the supersc... | 2 | {
"title": "Computational Exploration of Ambiphilic Reactivity of Azides and Sustmann's Paradigmatic Parabola",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00239",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00239"
} | 0 | |
What is the canonical SMILES of R1? | [
"C1(N2CCCC2)=CCCC1",
"C1=C(N2CCCC2)CCC1",
"C1=C(N2CCCC2)CCCC1",
"C1N(C2=CCCC2)CCC1"
] | 1 | {
"title": "Computational Exploration of Ambiphilic Reactivity of Azides and Sustmann's Paradigmatic Parabola",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00239",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00239"
} | 5 | |
What is the name of the reaction shown in Scheme 1? | [
"The reaction is a Diels–Alder reaction ([4+2] cycloaddition) of phenyl azide with various alkene/alkyne dipolar acceptors.",
"The reaction is a 1,3-nucleophilic addition (1,3-Nucleophilic Addition) of phenyl azide with various alkene/alkyne dipolar acceptors.",
"The reaction is a 1,2-dipolar cycloaddition (1,2... | 3 | {
"title": "Computational Exploration of Ambiphilic Reactivity of Azides and Sustmann's Paradigmatic Parabola",
"journal": "JOURNAL OF ORGANIC CHEMISTRY",
"doi": "10.1021/acs.joc.1c00239",
"url": "https://pubs.acs.org/doi/10.1021/acs.joc.1c00239"
} | 0 | |
How many nucleophilic aromatic substitution (S_NAr) reactions are there in this retrosynthetic route? Which steps are they, respectively? | [
"There are two nucleophilic aromatic substitution reactions:\n• First S_NAr: intermediate 11 reacts with 12 to give intermediate 9;\n• Second S_NAr: intermediate 13a/13b reacts with 14 to give intermediate 11.",
"There are three nucleophilic aromatic substitution reactions:\n• First S_NAr: intermediate 11 reacts ... | 0 | {
"title": "Synthesis of Adagrasib (MRTX849), a Covalent KRASG12C Inhibitor Drug for the Treatment of Cancer",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.2c04266",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c04266"
} | 4 | |
How was Adagrasib (1) retrosynthetically disassembled in Scheme 2? What were the two key intermediate structures obtained by the disconnection? | [
"In the first step of the retrosynthesis, Adagrasib (1) was split into cyano piperazine dihydrochloride (intermediate 12) and a pyrrolic alcohol derivative (intermediate 14).",
"In the first step of the retrosynthesis, Adagrasib (1) was split into a chloropyrimidine intermediate (intermediate 13a) and a pyrrolic ... | 3 | {
"title": "Synthesis of Adagrasib (MRTX849), a Covalent KRASG12C Inhibitor Drug for the Treatment of Cancer",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.2c04266",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c04266"
} | 4 | |
In the two-step S_NAr reaction, at which positions do intermediate 13 and intermediate 11 respectively undergo nucleophilic aromatic substitution with 14 and 12? | [
"The chlorine on the aryl ring of intermediate 13 is substituted by the amino group of 12 to give intermediate 11; whereas the sulfonyl group on the aryl ring of intermediate 11 is substituted by the hydroxy group of 14 to give intermediate 9 and water.",
"The chlorine or sulfonyl group on the aryl ring of interm... | 1 | {
"title": "Synthesis of Adagrasib (MRTX849), a Covalent KRASG12C Inhibitor Drug for the Treatment of Cancer",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.2c04266",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c04266"
} | 2 | |
What nucleophiles are used in this scheme? Which functional groups do they each introduce into the molecular scaffold? | [
"The nucleophiles used are:\n• Sodium cyanoacrylate (10), which introduces an acrylate and a fluorine atom;\n• Cyanomethylpiperazine hydrochloride (12), which introduces a terminal cyano group and a piperidine scaffold.",
"The nucleophiles used are:\n• Cyanomethylpiperazine hydrochloride (12), which introduces a ... | 1 | {
"title": "Synthesis of Adagrasib (MRTX849), a Covalent KRASG12C Inhibitor Drug for the Treatment of Cancer",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.2c04266",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c04266"
} | 1 | |
Which compound is the starting material of the reaction? | [
"9",
"11",
"17",
"Adagrasib (1)"
] | 2 | {
"title": "Synthesis of Adagrasib (MRTX849), a Covalent KRASG12C Inhibitor Drug for the Treatment of Cancer",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.2c04266",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.2c04266"
} | 0 | |
Please briefly describe the overall reaction process of this electrochemical coupling reaction, including the reactants, products, and the main reaction conditions. | [
"This reaction couples a benzyl compound (substrate 1) with benzylamine (2a) under electrochemical conditions with a graphite anode and a platinum cathode to produce N-benzoylbenzylamine (3). The reaction is carried out in dichloromethane solvent at room temperature with a current of 10 mA passed until a total char... | 1 | {
"title": "Electrochemical Benzylic C(sp3)-H Direct Amidation",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c04012",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04012"
} | 2 | |
What aryl ring substituents were introduced on substrate 1 in different examples? Please list at least three and state the corresponding yields. | [
"The aryl ring substituents on substrate 1 and the corresponding yields include:\n- para-diphenyl substitution (3f), yield 19%;\n- para-methoxy substitution (3d), yield 80%;\n- meta-tert-butyl substitution (3a), yield 73%.",
"The aryl ring substituents on substrate 1 and the corresponding yields include:\n- meta-... | 3 | {
"title": "Electrochemical Benzylic C(sp3)-H Direct Amidation",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c04012",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04012"
} | 0 | |
What is the SMILES of the product with the highest yield? | [
"c1(C(=O)NC(C)c2ccc(OC)cc2)ccccc1",
"c1(C(=O)NC2CCc3ccccc32)ccccc1",
"c1(C(=O)NC(C)c2cccc(C(C)(C)C)c2)ccccc1",
"c1(C(=O)NC(C)c2ccc(CC)cc2)ccccc1"
] | 0 | {
"title": "Electrochemical Benzylic C(sp3)-H Direct Amidation",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c04012",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04012"
} | 5 | |
What is the structure of the substrate corresponding to product 3h? What is the yield of this example? | [
"The substrate corresponding to product 3h is indane (C9H10), which, when coupled with benzamide, gives N-(indan-1-yl)benzamide. The isolated yield of this reaction is 53%.",
"The substrate corresponding to product 3h is 4-methoxyethylbenzene, which, when coupled with benzamide, gives N-(1-(4-methoxyphenyl)ethyl)... | 3 | {
"title": "Electrochemical Benzylic C(sp3)-H Direct Amidation",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c04012",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04012"
} | 0 | |
What is the yield when ethylbenzene is used as the substrate? | [
"63%",
"42%",
"38%",
"80%"
] | 1 | {
"title": "Electrochemical Benzylic C(sp3)-H Direct Amidation",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c04012",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c04012"
} | 0 | |
How does the oxidation state of Mo change at each stage in this SOMC catalytic system? Please analyze in conjunction with the illustration. | [
"In the SOMC route, Mo in the initial precursor is in the +VI oxidation state and is chemically reduced by one electron to become a +V reduced precatalyst; subsequently, upon reaction with the olefin substrate, Mo is further reduced back to +III to form the alkylidene active site.",
"In the SOMC route, Mo in the ... | 3 | {
"title": "Olefin-Surface Interactions: A Key Activity Parameter in Silica-Supported Olefin Metathesis Catalysts",
"journal": "JACS AU",
"doi": "10.1021/jacsau.2c00052",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.2c00052"
} | 2 | |
Please describe in detail the process and required conditions in the SOMC route from the surface organometallic precursor (≡SiO)2Mo(=O)2 to the formation of the active catalyst? | [
"First anchor the precursor (≡SiO)2Mo(=O)2 on the SiO2 surface, add 2 equivalents of reductant to reduce Mo from oxidation state VI to V, obtaining the reduced precatalyst. React with an olefin substrate at low temperature (<100°C) to form a surface Mo alkenyl compound, which is the active catalyst in the reaction ... | 3 | {
"title": "Olefin-Surface Interactions: A Key Activity Parameter in Silica-Supported Olefin Metathesis Catalysts",
"journal": "JACS AU",
"doi": "10.1021/jacsau.2c00052",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.2c00052"
} | 2 | |
What are the similarities and differences between the metal alkylidene compounds shown in (c) and (d) in the figure? | [
"Both are neutral Mo(IV) alkylidyne compounds, coordinated with an NHC ancillary ligand and a B(ArF)4- anion; (c) is a molecular catalyst, completely dissolved in the medium, while (d) is a catalyst supported on SiO2.",
"Both are cationic Mo(imido) alkylidene complexes, having the same NHC ancillary ligand and B(... | 3 | {
"title": "Olefin-Surface Interactions: A Key Activity Parameter in Silica-Supported Olefin Metathesis Catalysts",
"journal": "JACS AU",
"doi": "10.1021/jacsau.2c00052",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.2c00052"
} | 3 | |
What precatalyst is obtained at the end of the conventional impregnation route (incipient wetness impregnation) shown in the figure? | [
"A single cationic Mo+ (Mo+/SiO2) precursor catalyst supported on SiO2.",
"The (≡SiO)2Mo(=O)2–red precatalyst prepared by the surface organometallic chemistry route (precatalyst before reduction).",
"The MoOx/SiO2–ox precatalyst dispersed on SiO2 (precatalyst before reduction).",
"The MoOx/SiO2–red precatalys... | 3 | {
"title": "Olefin-Surface Interactions: A Key Activity Parameter in Silica-Supported Olefin Metathesis Catalysts",
"journal": "JACS AU",
"doi": "10.1021/jacsau.2c00052",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.2c00052"
} | 0 | |
Why is it easier to obtain high-activity alkenyl complexes when reacting with olefins at lower temperatures (<100°C)? | [
"Low temperature can reduce rearrangement of SiO₂ surface functional groups, keeping active sites open, thereby increasing the alkenylation reaction rate and stabilizing Mo–alkenyl complexes.",
"Low temperature can increase the electron density at the Mo center, promoting olefin coordination and insertion reactio... | 2 | {
"title": "Olefin-Surface Interactions: A Key Activity Parameter in Silica-Supported Olefin Metathesis Catalysts",
"journal": "JACS AU",
"doi": "10.1021/jacsau.2c00052",
"url": "https://pubs.acs.org/doi/10.1021/jacsau.2c00052"
} | 2 | |
Briefly describe the overall process of the reaction, including reactants, reagents, solvent, conditions, and products. | [
"Using a substituted dibenzo-4-seleno- or telluro-dihydropyridine (X = Se or Te) as the substrate, 2 equivalents of phenol as the coupling reagent, K₂CO₃ (1 eq.) as the base, ODCB (1,2-dichlorobenzene) as the solvent, reacting at 130 °C under an O₂ atmosphere for 2–6 h, achieving C–N coupling via C–H activation, an... | 3 | {
"title": "Dehydrogenative C-H Phenochalcogenazination",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.1c00573",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c00573"
} | 2 | |
In the selenium derivative series, when R1 = OMe, which example has the highest yield? What is its yield? | [
"In the selenium derivatives, the highest yield for R1 = OMe occurs in example PSeZ-11, with a yield of 87%.",
"In the selenium derivatives, the highest yield for R1 = OMe occurs in example PSeZ-9, with a yield of 87%.",
"In the selenium derivatives, the highest yield for R1 = OMe occurs in example PSeZ-16, wit... | 0 | {
"title": "Dehydrogenative C-H Phenochalcogenazination",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.1c00573",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c00573"
} | 0 | |
Inference question: Are the yields of the Te-series derivatives higher or lower compared to the Se-series? Please give possible reasons. | [
"The Te-series derivatives generally have slightly lower yields than the Se-series. It may be because organotellurium compounds are less stable, leading to decomposition of products or starting materials, and tellurium is also more easily oxidized by air than selenium, forming other byproducts.",
"The Te-series d... | 0 | {
"title": "Dehydrogenative C-H Phenochalcogenazination",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.1c00573",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c00573"
} | 3 | |
What is the title of the reaction shown in this figure? | [
"Dehydrogenative C–H Phenochalcogenazination with Selenium and Tellurium",
"Dehydrogenative C–H Phenothiazanization with Selenium and Tellurium",
"Oxidative C–H Phenochalcogenation with Selenium and Tellurium",
"Dehydrogenative C–H Phenochalcogenazination with Selenium and Sulfur"
] | 0 | {
"title": "Dehydrogenative C-H Phenochalcogenazination",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.1c00573",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c00573"
} | 0 | |
When the reaction substrate is unsubstituted phenol or naphthol, how does the yield change? | [
"When the reaction substrate is unsubstituted phenol or naphthol, the yield is slightly increased",
"When the reaction substrate is unsubstituted phenol or naphthol, the yield remains essentially unchanged",
"When the reaction substrate is unsubstituted phenol or naphthol, the yield decreases significantly",
... | 2 | {
"title": "Dehydrogenative C-H Phenochalcogenazination",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.1c00573",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.1c00573"
} | 3 | |
How many structurally different substrates were tested in the figure? | [
"10",
"7",
"9",
"6"
] | 1 | {
"title": "Synthesis of Cyclopropanes via Hydrogen-Borrowing Catalysis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c01768",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c01768"
} | 0 | |
Please describe in detail the overall reaction scheme shown in the figure, including the starting substrates, catalysts, reaction conditions and the structural features of the products. | [
"The reaction uses 4-aryloxybutanone derivatives (ArCO–CH2CH2CH2O–Ar', with various substituents possible on Ar') as the substrate, and under catalysis by [Ir(cod)Cl2] (1 mol%) and di(phenylphosphino)benzene (dppBz, 2 mol%), with addition of KOH (4 equiv) and excess benzyl alcohol (PhCH2OH, 10 equiv), at 110°C for ... | 1 | {
"title": "Synthesis of Cyclopropanes via Hydrogen-Borrowing Catalysis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c01768",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c01768"
} | 0 | |
Please write the Extended-SMILES representation of the reactant scaffold (without considering specific substituents), and indicate the definitions of each placeholder. | [
"Reactant scaffold E-SMILES: *C(=O)OCCCOc1ccccc1<sep><a>0:Ar</a><r>0:R</r> where '<a>0:Ar</a>' denotes an aryl acceptor position on the benzene ring, and '<r>0:R</r>' denotes a variable substituent R on the ketone alpha-carbon.",
"Reactant scaffold E-SMILES: *C(=O)CCCOc1ccccc1<sep><a>0:R</a><r>0:Ar</r> where '<a>... | 2 | {
"title": "Synthesis of Cyclopropanes via Hydrogen-Borrowing Catalysis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c01768",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c01768"
} | 5 | |
What are the catalytic system and additives used in this reaction? Please list each of their chemical names and amounts. | [
"[Ru(p-cymene)Cl2]2 (p-cymene dichloro ruthenium dimer, 1 mol%), dppBz (di(phenylphosphino)bibenzyl, 2 mol%) as the catalytic system, KOH (potassium hydroxide, 4 equivalents) as the base, benzyl alcohol (PhCH2OH, 10 equivalents) serving both as a proton donor and as a solvent additive.",
"[Ir(cod)Cl]2 (iridium cy... | 1 | {
"title": "Synthesis of Cyclopropanes via Hydrogen-Borrowing Catalysis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c01768",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c01768"
} | 1 | |
What is the product's E-SMILES general formula? | [
"*CC1(C(*)=O)CC1<sep><a>0:Ar</a><a>4:Ph</a>",
"*CC1(C(*)=O)CC1<sep><a>0:Ph</a><a>3:Ar</a>",
"*CC1(C(*)=O)CC1<sep><a>1:Ph</a><a>4:Ar</a>",
"*CC1(C(*)=O)CC1<sep><a>0:Ph</a><a>4:Ar</a>"
] | 3 | {
"title": "Synthesis of Cyclopropanes via Hydrogen-Borrowing Catalysis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c01768",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c01768"
} | 5 | |
From a structural point of view, how is substrate 1 transformed into product 3? Please briefly describe the (3+2+2) cyclization process. | [
"The cyclopropane-substituted alkene and alkyne in substrate 1 first coordinate to Co(I) in the Co-catalyzed system; the cyclopropane undergoes ring-opening insertion to generate a Co-alkyl intermediate, which then undergoes a [2+2] addition/cyclization with the R,R′-substituted alkene; finally, reductive eliminati... | 0 | {
"title": "Cobalt(I)-Catalyzed (3+2+2) Cycloaddition between Alkylidenecyclopropanes, Alkynes, and Alkenes",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c03511",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c03511"
} | 2 | |
How many different structures of Y are shown in the figure? | [
"4",
"8",
"6",
"10"
] | 0 | {
"title": "Cobalt(I)-Catalyzed (3+2+2) Cycloaddition between Alkylidenecyclopropanes, Alkynes, and Alkenes",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c03511",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c03511"
} | 0 | |
What are the specific reaction conditions for this reaction? Please list the catalyst, ligand, reductant, additive, solvent, temperature, and reaction time. | [
"The reaction was carried out in 1,2-dichloroethane (DCE), using CoBr2 (10 mol%) as the catalyst, dppp (1,3-bis(diphenylphosphino)propane, 12 mol%) as the ligand, Zn (5 mol%) and ZnBr2 (20 mol%) as the reductant/additive, heated at 110 °C for 16 hours.",
"The reaction was carried out in 1,2-dichloroethane (DCE), ... | 2 | {
"title": "Cobalt(I)-Catalyzed (3+2+2) Cycloaddition between Alkylidenecyclopropanes, Alkynes, and Alkenes",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c03511",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c03511"
} | 0 | |
What is the E-SMILES of product 3b? | [
"C=C1CC[C@H]2COCC2=C2CN(S(=O)(=O)c3ccc(C)cc3)C[C@@H]12<sep>",
"C=C1CC[C@@H]2COCC2=C2CN(S(=O)(=O)c3ccc(C)cc3)C[C@@H]12<sep>",
"C=C1CC[C@@H]2COCC2=C1CN(S(=O)(=O)c3ccc(C)cc3)C[C@@H]12<sep>",
"C=C1CC[C@@H]2COCC2=C2CN(S(=O)(=O)c3ccc(OMe)cc3)C[C@@H]12<sep>"
] | 1 | {
"title": "Cobalt(I)-Catalyzed (3+2+2) Cycloaddition between Alkylidenecyclopropanes, Alkynes, and Alkenes",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c03511",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c03511"
} | 5 | |
Which example products in the figure contain carboxylate ester substituents? Please list the corresponding X/E group types and their yields. | [
"Products containing carboxylate esters are:\n- 3c: X=C(CO₂Et)₂, yield 76%;\n- 3e: E=CO₂Me, yield 73%;\n- 3f: E=CO₂Et, yield 77%;\n- 3h: X=C(CO₂Et)₂, yield 64%;\n- 3k: R=CO₂Me, yield 0%;\n- 3n: X=C(CO₂Et)₂, yield 59%.",
"Products containing carboxylate esters are:\n- 3c: X=C(CO₂Et)₂, yield 76%;\n- 3e: E=CO₂Et, yi... | 0 | {
"title": "Cobalt(I)-Catalyzed (3+2+2) Cycloaddition between Alkylidenecyclopropanes, Alkynes, and Alkenes",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c03511",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c03511"
} | 0 | |
In the competition experiment of aryl–SiMe₃/aryl–Bpin versus aryl–GeEt₃ in Scheme 1b, why is only the aryl–GeEt₃ nitrated while the other two remain unreactive? | [
"In the photocatalytic system, the GeEt₃ substituent has the lowest electrochemical oxidation potential and is most easily oxidized to form aryl radicals or cationic intermediates, initiating nitration; whereas the SiMe₃ and Bpin substituents have higher oxidation potentials and are not easily oxidized, so they rem... | 3 | {
"title": "Site-Selective Nitration of Aryl Germanes at Room Temperature",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c02822",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02822"
} | 3 | |
In the experiment producing product 2 (ortho-fluoro-substituted aryl nitro compound), what effect would occur if NaBF₄ is not added? | [
"If NaBF₄ is not added, the yield of product 2 will decrease from 70% to 28%.",
"If NaBF₄ is not added, the yield of product 2 will increase from 70% to 92%.",
"If NaBF₄ is not added, the yield of product 2 remains unchanged, staying at about 70%.",
"If NaBF₄ is not added, the yield of product 2 will decrease... | 0 | {
"title": "Site-Selective Nitration of Aryl Germanes at Room Temperature",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c02822",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02822"
} | 1 | |
Please describe this reaction general formula in words, including the main reactant, the nitro source, and the product, as well as the main reagents and conditions. | [
"Using aryl triethylgermane (Ar–GeEt₃) as the substrate, and N-nitrosuccinimide (N-nitrosuccinimide) under blue LED irradiation, in MeCN solution at room temperature, in the cooperative presence of Ru(bpy)₃(PF₆)₂ (2.5 mol%) and NaBF₄ (1.5 equiv), reacted for 16 h, the Ar–Ge bond can be cleaved and a –NO₂ group intr... | 0 | {
"title": "Site-Selective Nitration of Aryl Germanes at Room Temperature",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c02822",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02822"
} | 0 | |
What is the title of the chemical reaction study shown in this figure (Scheme 1)? | [
"Study of intermolecular competition and site-selectivity in aryl germane nitration",
"Study of site-selectivity and orthogonality of aryl germane ipso-nitration",
"Study of C–N bond selectivity and orthogonality in aryl germane ipso-nitration",
"Study of site-selectivity and regioselectivity of aryl germane ... | 1 | {
"title": "Site-Selective Nitration of Aryl Germanes at Room Temperature",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c02822",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02822"
} | 0 | |
Which of the following statements about the key additives and conditions used in this C–Ge bond ipso-nitration reaction is correct? | [
"Ru(bpy)₃(PF₆)₂ as the photocatalyst, excited under a UV LED to generate a Ru³⁺*/Ru⁴⁺ cycle; NaBF₄ as an additive provides BF₄⁻ to assist activation of the C–Cl bond, forming a five-coordinate germanium intermediate to promote bond cleavage; MeCN as a polar non-protic solvent is favorable for stabilizing charged in... | 3 | {
"title": "Site-Selective Nitration of Aryl Germanes at Room Temperature",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.3c02822",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.3c02822"
} | 1 | |
Please briefly describe the typical reaction process shown in Scheme 2, including the reactants, products, catalyst, solvent, and reaction conditions. | [
"Scheme 2 shows that using di-alkynyl amide (1) and 3,5-dimethylisoxazole (2a) as substrates, with 10 mol% PPh3AuCl/AgNTf2 as catalyst, in dichloromethane (DCM) at 75 °C for 20 h, the tricyclic heterocyclic products of series 3 are formed in yields ranging from 27% to 68%.",
"Scheme 2 shows that using di-alkynyl ... | 2 | {
"title": "An Intramolecular Reaction between Pyrroles and Alkynes Leads to Pyrrole Dearomatization under Cooperative Actions of a Gold Catalyst and Isoxazole Cocatalysts",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c02601",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c02601"
} | 0 | |
What are the N-substituents (R₁) of products 3a–3d shown in the figure? What are the corresponding yields and dr values? | [
"3a: R₁ = Me, yield 68%; 3b: R₁ = n-Bu, yield 53%, dr = 2.2:1; 3c: R₁ = i-Pr, yield 53%, dr = 1.8:1; 3d: R₁ = Bn, yield 51%, dr = 2.5:1",
"3a: R₁ = Me, yield 68%; 3b: R₁ = n-Bu, yield 53%, dr = 1.2:1; 3c: R₁ = i-Pr, yield 53%, dr = 2.0:1; 3d: R₁ = Bn, yield 51%, dr = 2.5:1 (and the stereochemistry was determined ... | 1 | {
"title": "An Intramolecular Reaction between Pyrroles and Alkynes Leads to Pyrrole Dearomatization under Cooperative Actions of a Gold Catalyst and Isoxazole Cocatalysts",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c02601",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c02601"
} | 0 | |
What is the E-SMILES of substrate 2a? | [
"Cc1cc(N)on1<sep>",
"Cc1cnc(C)o1<sep>",
"Cc1cc(C)on1<sep>",
"Cc1cc(C)oc1<sep>"
] | 2 | {
"title": "An Intramolecular Reaction between Pyrroles and Alkynes Leads to Pyrrole Dearomatization under Cooperative Actions of a Gold Catalyst and Isoxazole Cocatalysts",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c02601",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c02601"
} | 5 | |
Which explanation about the effect of R⁴/R⁵ substituents on the yields of products 3m–3p is correct? | [
"Cl and Br, as electron donors, enhance alkyne reactivity (3n yield 47%, 3p yield 30%), and Br's smaller steric hindrance makes the yield highest; thus this supports the electron-donating effect.",
"Me, as an electron donor, can enhance alkyne reactivity (3m yield 56%), while Cl and Br, as electron-withdrawing gr... | 1 | {
"title": "An Intramolecular Reaction between Pyrroles and Alkynes Leads to Pyrrole Dearomatization under Cooperative Actions of a Gold Catalyst and Isoxazole Cocatalysts",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c02601",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c02601"
} | 3 | |
Which of the following statements about the structural characteristics of substrate 2a and its role in this gold-catalyzed cyclization reaction is correct? | [
"Substrate 2a is 3,5-dimethylisoxazole; the five-membered ring contains an active C=N–O, and the strongly nucleophilic O can act as a nucleophile to attack the Au(I)-activated alkyne intermediate, thereby constructing a new O-heterocyclic framework and completing the cyclization.",
"Substrate 2a is 3,5-dimethylfu... | 2 | {
"title": "An Intramolecular Reaction between Pyrroles and Alkynes Leads to Pyrrole Dearomatization under Cooperative Actions of a Gold Catalyst and Isoxazole Cocatalysts",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c02601",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c02601"
} | 1 | |
Please briefly describe the overall objective of this synthetic scheme and the main intermediate structures involved | [
"This scheme uses (R)-geraniol as the starting material, undergoes chlorination, hydroxylation and oxidative dehydrogenation to generate a diketone intermediate, then undergoes radical acid-directed lactic lactonization to construct the core scaffold, and finally obtains Scaffold 2 via an oxy-Cope rearrangement. Ke... | 2 | {
"title": "Expanding Natural Diversity: Tailored Enrichment of the 8,12-Sesquiterpenoid Lactone Chemical Space through Divergent Synthesis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c01374",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c01374"
} | 4 | |
What is the origin of the high site-selectivity of acid-directed radical lactylation? | [
"The high selectivity of acid-directed lactylation arises from the direct complexation of the substrate carboxylic acid with iodine radicals to form a stable intermediate; at the same time, PIDA, as a reductant, can rapidly supply radicals, and high light intensity can accelerate radical generation, thereby prefere... | 2 | {
"title": "Expanding Natural Diversity: Tailored Enrichment of the 8,12-Sesquiterpenoid Lactone Chemical Space through Divergent Synthesis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c01374",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c01374"
} | 2 | |
Which reagents and conditions were used in step 5? What class of reaction mechanism does this step belong to? | [
"Step 5 was carried out using silver nitrate (AgNO3) and iodine (I2) under light irradiation, and it is an electrophilic epoxidation reaction.",
"Step 5 was carried out using di(acetoxy)iodine (PIDA) and iodine (I2) under light irradiation, and it is a radical acid-directed lactonization (radical lactonization) r... | 1 | {
"title": "Expanding Natural Diversity: Tailored Enrichment of the 8,12-Sesquiterpenoid Lactone Chemical Space through Divergent Synthesis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c01374",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c01374"
} | 1 | |
Which step's reaction conditions are the most stringent? | [
"12",
"11",
"5",
"9"
] | 1 | {
"title": "Expanding Natural Diversity: Tailored Enrichment of the 8,12-Sesquiterpenoid Lactone Chemical Space through Divergent Synthesis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c01374",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c01374"
} | 3 | |
Why does a dehydration side product form and the expected rearrangement product fail to be obtained when attempting the anionic Oxy-Cope rearrangement? | [
"When strong bases such as KHMDS are used, the base first deprotonates the ester group to generate a stable ester salt, inhibiting the enolization process and causing the substrate to be more prone to dehydration via a β-elimination pathway; the resulting ester-salt intermediate also reduces the reaction rate of th... | 2 | {
"title": "Expanding Natural Diversity: Tailored Enrichment of the 8,12-Sesquiterpenoid Lactone Chemical Space through Divergent Synthesis",
"journal": "ORGANIC LETTERS",
"doi": "10.1021/acs.orglett.4c01374",
"url": "https://pubs.acs.org/doi/10.1021/acs.orglett.4c01374"
} | 2 |
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