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rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate
The title molecule, C(20)H(23)NO(7), the product of nucleophilic cleavage of the 3a,6-epoxy bridge in 1-oxo-2-phenyloctahydro-3a,6-epoxyisoindole-7-carboxylate, comprises a cis-fused bicyclic system containing a 2-pyrrolidinone ring in an envelope conformation (with the C atom bearing the car...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3790418/ https://www.ncbi.nlm.nih.gov/pubmed/24098237 http://dx.doi.org/10.1107/S1600536813025129 |
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author | Toze, Flavien A. A. Nikitina, Eugeniya V. Zaytsev, Vladimir P. Zubkov, Fedor I. Khrustalev, Victor N. |
author_facet | Toze, Flavien A. A. Nikitina, Eugeniya V. Zaytsev, Vladimir P. Zubkov, Fedor I. Khrustalev, Victor N. |
author_sort | Toze, Flavien A. A. |
collection | PubMed |
description | The title molecule, C(20)H(23)NO(7), the product of nucleophilic cleavage of the 3a,6-epoxy bridge in 1-oxo-2-phenyloctahydro-3a,6-epoxyisoindole-7-carboxylate, comprises a cis-fused bicyclic system containing a 2-pyrrolidinone ring in an envelope conformation (with the C atom bearing the carboxylate substituent as the flap) and a cyclohexane ring in a chair conformation. The carboxylate substituent occupies the equatorial position, whereas the two acetyloxy substituents are in axial positions. The N atom has a trigonal-planar geometry, the sum of the bond angles being 359.3 (3)°. The dihedral angle between the mean plane of the four planar atoms of the pyrrolidinone ring and the phenyl ring is 25.98 (6)°. In the crystal, molecules are linked into zigzag chains along the c-axis direction by C—H⋯O hydrogen bonds. |
format | Online Article Text |
id | pubmed-3790418 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-37904182013-10-04 rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate Toze, Flavien A. A. Nikitina, Eugeniya V. Zaytsev, Vladimir P. Zubkov, Fedor I. Khrustalev, Victor N. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title molecule, C(20)H(23)NO(7), the product of nucleophilic cleavage of the 3a,6-epoxy bridge in 1-oxo-2-phenyloctahydro-3a,6-epoxyisoindole-7-carboxylate, comprises a cis-fused bicyclic system containing a 2-pyrrolidinone ring in an envelope conformation (with the C atom bearing the carboxylate substituent as the flap) and a cyclohexane ring in a chair conformation. The carboxylate substituent occupies the equatorial position, whereas the two acetyloxy substituents are in axial positions. The N atom has a trigonal-planar geometry, the sum of the bond angles being 359.3 (3)°. The dihedral angle between the mean plane of the four planar atoms of the pyrrolidinone ring and the phenyl ring is 25.98 (6)°. In the crystal, molecules are linked into zigzag chains along the c-axis direction by C—H⋯O hydrogen bonds. International Union of Crystallography 2013-09-18 /pmc/articles/PMC3790418/ /pubmed/24098237 http://dx.doi.org/10.1107/S1600536813025129 Text en © Toze et al. 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Toze, Flavien A. A. Nikitina, Eugeniya V. Zaytsev, Vladimir P. Zubkov, Fedor I. Khrustalev, Victor N. rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate |
title |
rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate |
title_full |
rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate |
title_fullStr |
rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate |
title_full_unstemmed |
rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate |
title_short |
rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate |
title_sort | rac-methyl (3ar*,4s*,5r*,7ar*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1h-isoindole-4-carboxylate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3790418/ https://www.ncbi.nlm.nih.gov/pubmed/24098237 http://dx.doi.org/10.1107/S1600536813025129 |
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