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Heterocyclic Compounds

Heterocyclic compounds are a class of compounds that consist of carbon atoms and non-carbon atoms altogether forming a cyclic skeletal structure. These non-carbon atoms are collectively referred to as a heteroatom. The common heteroatoms include nitrogen, oxygen, and sulfur. Lactones, lactams, cyclic ethers that we’ve already learned are heterocyclic compounds. With similar properties of congeneric open-chain compounds, they will be discussed in corresponding chapters. This chapter will mainly discuss heterocyclic compounds with relatively stable ring system and with a certain degree of aromaticity, also known as aromatic heterocyclic compound.

There are many kinds and a large number of heterocyclic compounds widely distributed in nature. Many natural heterocyclic compounds in animals and plants play an important physiological role in the body. For example, heterocyclic structure exists in chlorophyll in plants, hemoglobin in animal blood, alkaloids and glycosides as the active ingredient in herbs, some antibiotics and vitamins, certain composition of amino acids in protein and bases in nucleotide. About half of the existing medicines have heterocyclic structures. Thus, heterocyclic compounds play an important role in organic compounds especially in organic medicines.

The most common and also the most important heterocyclic compounds are that with five-membered or six-membered heterocyclic ring and their fused heterocyclic compounds. Therefore, according to the size of the ring, heterocyclic compounds can be divided into five-membered compounds and six-membered heterocyclic compounds. E.g., furan, thiophene, pyrrole, imidazole, triazole and their fused heterocyclic compounds, indole, benzimidazole and diphenylene-oxide are all five-membered heterocyclic compounds, while pyridine, pyrimidine and their fused heterocyclic compounds, quinoline and quinazoline are all six-membered heterocyclic compounds.

According to the number of hetero atoms, five-membered compounds and six-membered heterocyclic compounds can be divided into one-hetero-atom-containing heterocyclic compounds and two-hetero-atom-containing and several-hetero-atom-containing heterocyclic compounds. E.g., furan, thiophene, pyridine, indole, quinoline, dibenzofuran, etc. are one-hetero-atom-containing heterocyclic compounds; imidazole, pyrimidine, benzimidazole, quinazoline, etc. are two-hetero-atom-containing heterocyclic compounds; purine, comprising more than two hetero atoms, is a several-hetero-atom-containing heterocyclic compound. According to the form of the ring in the molecule, heterocyclic compounds can be divided into single-heterocyclic compounds and fused heterocyclic compounds. E.g., furan, pyridine, pyrimidine, imidazole, etc. are single-heterocyclic compounds and indole, quinoline, dibenzofuran, purines, etc. are fused heterocyclic compounds.

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Structure Chemical Name CAS MF
2-PYRROLIDIN-2-YLPYRIDINE 2-PYRROLIDIN-2-YLPYRIDINE 22083-78-9 C9H12N2
1-(3-HydroxyMethyl-pyrrolidin-1-yl)-ethanone 1-(3-HydroxyMethyl-pyrrolidin-1-yl)-ethanone 191347-96-3 C7H13NO2
Isopropyl-(4-Methyl-pyriMidin-2-yl)-aMine Isopropyl-(4-Methyl-pyriMidin-2-yl)-aMine 1341073-92-4 C8H13N3
Ethyl 4-Methyl-2-(Methylthio)-6-oxo-1,6-dihydropyriMidine-5-carboxylate Ethyl 4-Methyl-2-(Methylthio)-6-oxo-1,6-dihydropyriMidine-5-carboxylate 344361-90-6 C9H12N2O3S
5-(2-AMinopropyl)indole 5-(2-AMinopropyl)indole 3784-30-3 C11H14N2
IMidazo[1,2-a]pyridin-8-aMine, 7-broMo- IMidazo[1,2-a]pyridin-8-aMine, 7-broMo- 1357945-44-8 C7H6BrN3
1,3-Pyrrolidinedicarboxylic acid, 4-oxo-, 1-(1,1-diMethylethyl) 3-Methyl ester 1,3-Pyrrolidinedicarboxylic acid, 4-oxo-, 1-(1,1-diMethylethyl) 3-Methyl ester 194924-95-3 C11H17NO5
tert-butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate tert-butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate 1211586-14-9 C12H22N2O2
(S)-4-Oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid (S)-4-Oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid 1190392-22-3 C8H8N2O3
1-Methyl-5-oxo-L-Proline 1-Methyl-5-oxo-L-Proline 52574-06-8 C6H9NO3
3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione 1239986-50-5 C23H19N3O2
5-chloro-7-(3,4-diMethoxyphenyl)iMidazo[1,2-c]pyriMidine 5-chloro-7-(3,4-diMethoxyphenyl)iMidazo[1,2-c]pyriMidine 371171-20-9 C14H12ClN3O2
BenzaMide, N-[2-[[(3R,4R)-1-[cis-4-(1,3-benzodioxol-5-yl)-4-hydroxycyclohexyl]-4-ethoxy-3-pyrrolidinyl]aMino]-2-oxoethyl]-3-(trifluoroMethyl)-, rel- BenzaMide, N-[2-[[(3R,4R)-1-[cis-4-(1,3-benzodioxol-5-yl)-4-hydroxycyclohexyl]-4-ethoxy-3-pyrrolidinyl]aMino]-2-oxoethyl]-3-(trifluoroMethyl)-, rel- 1285539-85-6 C29H34F3N3O6
2,4-Dichloro-6-isopropyl-5,6-dihydropyrrolo[3,4-d]pyriMidin-7-one 2,4-Dichloro-6-isopropyl-5,6-dihydropyrrolo[3,4-d]pyriMidin-7-one 1079649-94-7 C9H9Cl2N3O
(2-BENZOTHIAZOLYLTHIO)ACETIC ACID (2-BENZOTHIAZOLYLTHIO)ACETIC ACID 6295-57-4 C9H7NO2S2
3-[[3,5-bis(trifluoroMethyl)phenyl]aMino]-4-[[(1S,2S)-2-(1-pyrrolidinyl)cyclohexyl]aMino]- 3-[[3,5-bis(trifluoroMethyl)phenyl]aMino]-4-[[(1S,2S)-2-(1-pyrrolidinyl)cyclohexyl]aMino]- 1211565-10-4 C22H23F6N3O2
2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3R,4R)-rel- 2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3R,4R)-rel- 905853-99-8 C23H19N3O2
CyclopentaneMethanol, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-7-yl)-2-hydroxy-, (1S,2S,4R)- CyclopentaneMethanol, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-7-yl)-2-hydroxy-, (1S,2S,4R)- 1113025-27-6 C12H14ClN3O2
Sulfuric acid, mono[(1R,2S,5R)-7-oxo-2-[[[(3S)-3-pyrrolidinyloxy]amino]carbonyl]-1,6-diazabicyclo[3.2.1]oct-6-yl] ester Sulfuric acid, mono[(1R,2S,5R)-7-oxo-2-[[[(3S)-3-pyrrolidinyloxy]amino]carbonyl]-1,6-diazabicyclo[3.2.1]oct-6-yl] ester 1452458-72-8 C11H18N4O7S
Tramazoline Tramazoline 1082-57-1 C13H17N3
5-Bromo-1,3-dimethyl-1H-pyrazole 5-Bromo-1,3-dimethyl-1H-pyrazole 5744-70-7 C5H7BrN2
5,6,7,8,9,10-hexahydrocycloocta[b]pyridine 5,6,7,8,9,10-hexahydrocycloocta[b]pyridine 28712-60-9 C11H15N
1,3-Benzenedicarboxylic acid, 4,6-di-1H-imidazol-1-yl- 1,3-Benzenedicarboxylic acid, 4,6-di-1H-imidazol-1-yl- 2374700-80-6 C14H10N4O4
2-(4-methoxyphenyl)-2-pyrrolidin-1-ylacetonitrile 2-(4-methoxyphenyl)-2-pyrrolidin-1-ylacetonitrile 15190-12-2 C13H16N2O
5-methyl-2-phenyl-1H-imidazole-4-carboxylic acid 5-methyl-2-phenyl-1H-imidazole-4-carboxylic acid 28824-94-4 C11H10N2O2
dichlorobis(3-pyridylcarboxamide-N1)cobalt dichlorobis(3-pyridylcarboxamide-N1)cobalt 6856-47-9 C12H12Cl2CoN4O2
(S)-3-methyl-2-(pyrrolidin-2-yl)pyridine (S)-3-methyl-2-(pyrrolidin-2-yl)pyridine 1213567-87-3 C10H14N2
4,4'-((2-methyl-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine 4,4'-((2-methyl-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine 2446431-88-3 C21H18N2
1-benzyl-4-pyrrolidin-1-ylpiperidine, dihydrochloride 1-benzyl-4-pyrrolidin-1-ylpiperidine, dihydrochloride 4983-38-4 C16H26Cl2N2
1-Methyl-1,2,3-triazole 1-Methyl-1,2,3-triazole 16681-65-5 C3H5N3
(2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid (2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid 21156-44-5 C5H8FNO2
(2S,5R)-7-oxo-2-((((R)-pyrrolidin-3-yl)oxy)carbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate (2S,5R)-7-oxo-2-((((R)-pyrrolidin-3-yl)oxy)carbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate 1452458-70-6 C11H18N4O7S
1H-Benzimidazole, 2,2',2'',2'''-[1,1'-biphenyl]-3,3',5,5'-tetrayltetrakis- 1H-Benzimidazole, 2,2',2'',2'''-[1,1'-biphenyl]-3,3',5,5'-tetrayltetrakis- 1572338-07-8 C40H26N8
Pyridine, 5-chloro-2-(chloromethyl)-3-[[[tris(1-methylethyl)silyl]oxy]methyl]- Pyridine, 5-chloro-2-(chloromethyl)-3-[[[tris(1-methylethyl)silyl]oxy]methyl]- 1456803-67-0 C16H27Cl2NOSi
1928707-64-5 1928707-64-5 1928707-64-5 C14H14FN5O2
3-Phenyl-1H-pyrazole 3-Phenyl-1H-pyrazole 2458-26-6 C9H8N2
1H-Pyrazole-3-carboxamide, 4-[5-[1,5-dihydro-3-[[(2-hydroxyethyl)amino]carbonyl]-5-oxo-1-(tetrahydro-1,1-dioxido-3-thienyl)-4H-pyrazol-4-ylidene]-1,3-pentadien-1-yl]-5-hydroxy-N-(2-hydroxyethyl)-1-(tetrahydro-1,1-dioxido-3-thienyl)-, sodium salt (1:1) 1H-Pyrazole-3-carboxamide, 4-[5-[1,5-dihydro-3-[[(2-hydroxyethyl)amino]carbonyl]-5-oxo-1-(tetrahydro-1,1-dioxido-3-thienyl)-4H-pyrazol-4-ylidene]-1,3-pentadien-1-yl]-5-hydroxy-N-(2-hydroxyethyl)-1-(tetrahydro-1,1-dioxido-3-thienyl)-, sodium salt (1:1) 1020729-05-8 C25H33N6NaO10S2
Benzene, 1-chloro-4-(methoxymethoxy)-2-methyl- Benzene, 1-chloro-4-(methoxymethoxy)-2-methyl- 928025-22-3 C9H11ClO2
(S)-4-iodo-1-(pyrrolidin-3-yl)-1H-pyrazole (S)-4-iodo-1-(pyrrolidin-3-yl)-1H-pyrazole
 4-(4-Bromophenyl)-4-piperidinol 4-(4-Bromophenyl)-4-piperidinol 57988-58-6 C11H14BrNO
1,3-Benzenedicarboxylic acid, 5-[(5-pyrimidinylcarbonyl)amino]- 1,3-Benzenedicarboxylic acid, 5-[(5-pyrimidinylcarbonyl)amino]- 1973826-31-1 C13H9N3O5
1-Ethyl-1H-iMidazole-5-carboxylic acid 1-Ethyl-1H-iMidazole-5-carboxylic acid 71925-11-6 C6H8N2O2
4-Hydroxy-6-Methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile 4-Hydroxy-6-Methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile 67643-17-8 C7H6N2O2
N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]-Thiourea N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]-Thiourea 1314743-49-1 C19H23F6N3S
L-Proline sodiuM salt L-Proline sodiuM salt 15383-56-9 C5H10NNaO2
1H-BenziMidazole-1-acetaMide, 2-phenyl-N-(phenylMethyl)-α-4-piperidinyl- 1H-BenziMidazole-1-acetaMide, 2-phenyl-N-(phenylMethyl)-α-4-piperidinyl- 1440753-53-6 C27H28N4O
4-Methyl-2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-benzonitrile 4-Methyl-2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-benzonitrile 863868-22-8 C14H18BNO2
5-(Pyrrolidin-1-yl)pentan-1-aMine dihydrochloride 5-(Pyrrolidin-1-yl)pentan-1-aMine dihydrochloride 1624260-73-6 C9H22Cl2N2
(2S)-2-(3-BROMOPHENYL)PYRROLIDINE (2S)-2-(3-BROMOPHENYL)PYRROLIDINE 1217694-15-9 C10H12BrN
2-AMino-3-(pyrrolidin-3-yl)propanoic acid 2-AMino-3-(pyrrolidin-3-yl)propanoic acid 1313016-75-9 C7H14N2O2
6-Methoxy-iMidazo[1,2-b]pyridazine-2-carboxylic acid 6-Methoxy-iMidazo[1,2-b]pyridazine-2-carboxylic acid 64068-09-3 C8H7N3O3
4,4',4''-(1,3,5-Triazine-2,4,6-triyl)trianiline 4,4',4''-(1,3,5-Triazine-2,4,6-triyl)trianiline 14544-47-9 C21H18N6
1-Ethyl-3-methylimidazolium bis(fluorosulfonyl)imide 1-Ethyl-3-methylimidazolium bis(fluorosulfonyl)imide 235789-75-0 C6H11F2N3O4S2
4-Bromo-1-pyrrolidin-3-yl-1H-pyrazole 4-Bromo-1-pyrrolidin-3-yl-1H-pyrazole 1247439-25-3 C7H10BrN3
2-(2-HYDROXYPHENYL)BENZOXAZOLE 2-(2-HYDROXYPHENYL)BENZOXAZOLE 835-64-3 C13H9NO2
2-(2,6-dioxopiperidin-3-yl)-5-(3-(hydroxymethyl)pyrrolidin-1-yl)isoindoline-1,3-dione 2-(2,6-dioxopiperidin-3-yl)-5-(3-(hydroxymethyl)pyrrolidin-1-yl)isoindoline-1,3-dione 2412058-47-8
2-(1-TRITYL-1H-IMIDAZOL-4-YL)-ETHYLAMINE HYDRATE 2-(1-TRITYL-1H-IMIDAZOL-4-YL)-ETHYLAMINE HYDRATE 195053-92-0 C24H23N3
8-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 8-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 88751-05-7 C9H8N2O2
2,2'-Bioxazole, 4,4'-bis(4-fluorophenyl)-4,4',5,5'-tetrahydro-, (4S,4'S)- 2,2'-Bioxazole, 4,4'-bis(4-fluorophenyl)-4,4',5,5'-tetrahydro-, (4S,4'S)- 2567867-99-4 C18H14F2N2O2
1-(4-BROMOBENZYL)-1H-IMIDAZOLE 1-(4-BROMOBENZYL)-1H-IMIDAZOLE 72459-46-2 C10H9BrN2
Reaction mass of 2-ethyl-4-methyl-1H-imidazole-1-propiononitrile and 2-ethyl-5-methyl-1H-imidazole-1-propiononitrile Reaction mass of 2-ethyl-4-methyl-1H-imidazole-1-propiononitrile and 2-ethyl-5-methyl-1H-imidazole-1-propiononitrile 568591-00-4
9-phenyl-1,7-diazabicyclo[4.3.0]nona-2,4,6,8-tetraene 9-phenyl-1,7-diazabicyclo[4.3.0]nona-2,4,6,8-tetraene 92961-15-4 C13H10N2
2-Pyrrolidinone,3-(hydroxymethyl)-1-methyl-(9CI) 2-Pyrrolidinone,3-(hydroxymethyl)-1-methyl-(9CI) 577780-05-3 C6H11NO2
1H-Imidazole-1-aceticacid,alpha,2-dimethyl-(9CI) 1H-Imidazole-1-aceticacid,alpha,2-dimethyl-(9CI) 782414-84-0 C7H10N2O2
5-Bromo-1H-1,2,4-triazol-3-amine 5-Bromo-1H-1,2,4-triazol-3-amine 389122-08-1 C2H3BrN4
1H-Benzimidazole-2-methanol,5-chloro-1-methyl-(9CI) 1H-Benzimidazole-2-methanol,5-chloro-1-methyl-(9CI) 380177-22-0 C9H9ClN2O
2-Pyridinecarboxamide,N-2-pyrimidinyl-(9CI) 2-Pyridinecarboxamide,N-2-pyrimidinyl-(9CI) 848308-21-4 C10H8N4O
2-Bromo-N-ethyl-5-methoxybenzenamine 2-Bromo-N-ethyl-5-methoxybenzenamine 1491754-06-3 C9H12BrNO
1-(3-CHLOROPHENYL)IMIDAZOLE 1-(3-CHLOROPHENYL)IMIDAZOLE 51581-52-3 C9H7ClN2
L-Tyr-NCA L-Tyr-NCA 3415-08-5 C10H9NO4
N-(2-AMINO-4-TRIFLUOROMETHYLPHENYL)PYRROLIDINE N-(2-AMINO-4-TRIFLUOROMETHYLPHENYL)PYRROLIDINE 133184-80-2 C11H13F3N2
Pyridine, 2-(4,5-dihydro-2-oxazolyl)- (9CI) Pyridine, 2-(4,5-dihydro-2-oxazolyl)- (9CI) 119165-69-4 C8H8N2O
2-Pyrimidinemethanamine, 5-ethyl-4,6-dimethyl- 2-Pyrimidinemethanamine, 5-ethyl-4,6-dimethyl- 1340495-16-0 C9H15N3
Thieno[2,3-d]pyrimidine-6-carboxylic acid, 2,4-diamino- (9CI) Thieno[2,3-d]pyrimidine-6-carboxylic acid, 2,4-diamino- (9CI) 155087-28-8 C7H6N4O2S
Pyrimidine, 4-chloro-2-fluoro- (9CI) Pyrimidine, 4-chloro-2-fluoro- (9CI) 51422-00-5 C4H2ClFN2
tert-butyl2-(piperazin-1-yl)ethylcarbamate tert-butyl2-(piperazin-1-yl)ethylcarbamate 112758-89-1 C13H14N2
ethyl 5-nitro-2,6-dioxo-3H-pyrimidine-4-carboxylate ethyl 5-nitro-2,6-dioxo-3H-pyrimidine-4-carboxylate 52047-16-2 C7H7N3O6
2-Methylindoline 2-Methylindoline 6872-06-6 C9H11N
OXO-PYRROLIDIN-1-YL-ACETIC ACID OXO-PYRROLIDIN-1-YL-ACETIC ACID 49791-37-9 C6H9NO3
4-(1H-imidazol-1-yl)pyridine 4-(1H-imidazol-1-yl)pyridine 25700-16-7 C8H7N3
2-Bromo-1-methyl-1H-imidazole-4-carboxylic  acid 2-Bromo-1-methyl-1H-imidazole-4-carboxylic acid 852181-03-4 C5H5BrN2O2
5-(BROMOMETHYL)OXAZOLE 5-(BROMOMETHYL)OXAZOLE 127232-42-2 C4H4BrNO
CHEMBRDG-BB 4003804 CHEMBRDG-BB 4003804 99858-80-7 C11H15NO
4-chloro-5-methoxy-2-(4-pyridinyl)pyrimidine 4-chloro-5-methoxy-2-(4-pyridinyl)pyrimidine 133661-38-8 C10H8ClN3O
5,6,7,8-Tetrahydro-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester 5,6,7,8-Tetrahydro-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester 91476-82-3 C9H13N3O2
ethyl 4-amino-5-methylthieno[2,3-d]pyrimidine-6-carboxylate ethyl 4-amino-5-methylthieno[2,3-d]pyrimidine-6-carboxylate 60598-74-5 C10H11N3O2S
3,3'-Bi(1H-pyrazole) 3,3'-Bi(1H-pyrazole) 2384-02-3 C6H6N4
CHEMBRDG-BB 6423830 CHEMBRDG-BB 6423830 83490-13-5 C13H10N2O2
1,3 dimethyl-5fluoropyrazol fluoride 1,3 dimethyl-5fluoropyrazol fluoride C5H8F2N2
5-CYCLOPROPYL-3-TRIFLUOROMETHYL-1H-PYRAZOLE 5-CYCLOPROPYL-3-TRIFLUOROMETHYL-1H-PYRAZOLE 1027617-86-2 C7H7F3N2
1,3-pyrrolidinedicarboxylic acid, 4-methyl-, 1-(1,1-dimethylethyl) ester, (3r,4r)-rel- 1,3-pyrrolidinedicarboxylic acid, 4-methyl-, 1-(1,1-dimethylethyl) ester, (3r,4r)-rel- 1253791-53-5 C11H19NO4
4,4'-Bi-4H-1,2,4-triazole
4,4'-Bi-4H-1,2,4-triazole 16227-15-9 C4H4N6
1H-INDAZOLE-3-CARBALDEHYDE 1H-INDAZOLE-3-CARBALDEHYDE 5235-10-9 C8H6N2O
ethyl 2-ethyl-2-methylbutanoate ethyl 2-ethyl-2-methylbutanoate 19945-14-3 C9H18O2
2-(Aminomethyl)-1-Boc-piperidine 2-(Aminomethyl)-1-Boc-piperidine 370069-31-1 C11H22N2O2
Imidazo[1,2-a]pyridin-7-ol Imidazo[1,2-a]pyridin-7-ol 896139-85-8 C7H6N2O
1,3,5-Triazine 1,3,5-Triazine 290-87-9 C3H3N3
2,4,6-trimethyl-1,3,5-triazine 2,4,6-trimethyl-1,3,5-triazine 823-94-9 C6H9N3
2-Vinyl-1,3-dioxolane 2-Vinyl-1,3-dioxolane 3984-22-3 C5H8O2
2α-Formylpyrrolidine-1-carboxylic acid benzyl ester 2α-Formylpyrrolidine-1-carboxylic acid benzyl ester 71461-30-8 C13H15NO3
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