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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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Detalles Bibliográficos
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
Descripción
Sumario: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.