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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...

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Autores principales: Toze, Flavien A. A., Nikitina, Eugeniya V., Zaytsev, Vladimir P., Zubkov, Fedor I., Khrustalev, Victor N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
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.
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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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