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(4S,5R)-4-Benzyloxy-5-[4-(cyclohexanecarbonyl)phenyl]-1-(4-methoxybenzyl)pyrrolidin-2-one
The title compound, C(32)H(35)NO(4), is an unexpected product obtained in the SmI(2)-mediated radical cross-coupling of a lactam 2-pyridyl sulfone with an arone. The asymmetric unit contains two molecules. In both molecules, the core pyrrolidinone ring adopts an approximate envelope conformation (...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998611/ https://www.ncbi.nlm.nih.gov/pubmed/24826132 http://dx.doi.org/10.1107/S1600536814003638 |
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author | Gao, Yan-Jiao Ma, Jie Zheng, Xiao |
author_facet | Gao, Yan-Jiao Ma, Jie Zheng, Xiao |
author_sort | Gao, Yan-Jiao |
collection | PubMed |
description | The title compound, C(32)H(35)NO(4), is an unexpected product obtained in the SmI(2)-mediated radical cross-coupling of a lactam 2-pyridyl sulfone with an arone. The asymmetric unit contains two molecules. In both molecules, the core pyrrolidinone ring adopts an approximate envelope conformation (with the C atom bearling the benzyloxy substituent as the flap) and the cyclohexyl ring has a chair conformation. The relative orientation of the two substitutent groups at the 4- and 5-positions of the pyrrolidinone ring is anti in both molecules, with O(benzyloxy)—C—C—C(benzene) torsion angles of 150.8 (3) and 154.2 (2)°. In the crystal, C—H⋯O interactions involving carbonyl groups as acceptors lead to the formation of a tape motif propagating parallel to the a-axis direction. |
format | Online Article Text |
id | pubmed-3998611 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-39986112014-05-13 (4S,5R)-4-Benzyloxy-5-[4-(cyclohexanecarbonyl)phenyl]-1-(4-methoxybenzyl)pyrrolidin-2-one Gao, Yan-Jiao Ma, Jie Zheng, Xiao Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(32)H(35)NO(4), is an unexpected product obtained in the SmI(2)-mediated radical cross-coupling of a lactam 2-pyridyl sulfone with an arone. The asymmetric unit contains two molecules. In both molecules, the core pyrrolidinone ring adopts an approximate envelope conformation (with the C atom bearling the benzyloxy substituent as the flap) and the cyclohexyl ring has a chair conformation. The relative orientation of the two substitutent groups at the 4- and 5-positions of the pyrrolidinone ring is anti in both molecules, with O(benzyloxy)—C—C—C(benzene) torsion angles of 150.8 (3) and 154.2 (2)°. In the crystal, C—H⋯O interactions involving carbonyl groups as acceptors lead to the formation of a tape motif propagating parallel to the a-axis direction. International Union of Crystallography 2014-03-12 /pmc/articles/PMC3998611/ /pubmed/24826132 http://dx.doi.org/10.1107/S1600536814003638 Text en © Gao et al. 2014 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 Gao, Yan-Jiao Ma, Jie Zheng, Xiao (4S,5R)-4-Benzyloxy-5-[4-(cyclohexanecarbonyl)phenyl]-1-(4-methoxybenzyl)pyrrolidin-2-one |
title | (4S,5R)-4-Benzyloxy-5-[4-(cyclohexanecarbonyl)phenyl]-1-(4-methoxybenzyl)pyrrolidin-2-one |
title_full | (4S,5R)-4-Benzyloxy-5-[4-(cyclohexanecarbonyl)phenyl]-1-(4-methoxybenzyl)pyrrolidin-2-one |
title_fullStr | (4S,5R)-4-Benzyloxy-5-[4-(cyclohexanecarbonyl)phenyl]-1-(4-methoxybenzyl)pyrrolidin-2-one |
title_full_unstemmed | (4S,5R)-4-Benzyloxy-5-[4-(cyclohexanecarbonyl)phenyl]-1-(4-methoxybenzyl)pyrrolidin-2-one |
title_short | (4S,5R)-4-Benzyloxy-5-[4-(cyclohexanecarbonyl)phenyl]-1-(4-methoxybenzyl)pyrrolidin-2-one |
title_sort | (4s,5r)-4-benzyloxy-5-[4-(cyclohexanecarbonyl)phenyl]-1-(4-methoxybenzyl)pyrrolidin-2-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998611/ https://www.ncbi.nlm.nih.gov/pubmed/24826132 http://dx.doi.org/10.1107/S1600536814003638 |
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