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2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one
The title compound, C(19)H(19)NO(3)S, was produced by the self-reaction of N-cinnamyl-N-tosylacrylamide in the presence of palladium(II) acetate via an intramolecular C—C coupling reaction and C—H activation. There are two chiral C atoms in the molecule, but the crystal is a racemic system due t...
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/PMC3685075/ https://www.ncbi.nlm.nih.gov/pubmed/23795094 http://dx.doi.org/10.1107/S1600536813011045 |
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author | Wu, Min Hu, Yi-Min |
author_facet | Wu, Min Hu, Yi-Min |
author_sort | Wu, Min |
collection | PubMed |
description | The title compound, C(19)H(19)NO(3)S, was produced by the self-reaction of N-cinnamyl-N-tosylacrylamide in the presence of palladium(II) acetate via an intramolecular C—C coupling reaction and C—H activation. There are two chiral C atoms in the molecule, but the crystal is a racemic system due to a lack of chiral separation. The five-membered ring is twisted about the methylene–methane bond, and the cyclohexa-1,4-diene ring has a boat conformation. The dihedral angle between the benzene rings is 88.27 (14)°, indicating an almost orthogonal relationship and an approximate L-shape for the molecule. In the crystal, the presence of C—H⋯π interactions leads to inversion dimers. |
format | Online Article Text |
id | pubmed-3685075 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-36850752013-06-21 2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one Wu, Min Hu, Yi-Min Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(19)NO(3)S, was produced by the self-reaction of N-cinnamyl-N-tosylacrylamide in the presence of palladium(II) acetate via an intramolecular C—C coupling reaction and C—H activation. There are two chiral C atoms in the molecule, but the crystal is a racemic system due to a lack of chiral separation. The five-membered ring is twisted about the methylene–methane bond, and the cyclohexa-1,4-diene ring has a boat conformation. The dihedral angle between the benzene rings is 88.27 (14)°, indicating an almost orthogonal relationship and an approximate L-shape for the molecule. In the crystal, the presence of C—H⋯π interactions leads to inversion dimers. International Union of Crystallography 2013-05-18 /pmc/articles/PMC3685075/ /pubmed/23795094 http://dx.doi.org/10.1107/S1600536813011045 Text en © Wu and Hu 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 Wu, Min Hu, Yi-Min 2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one |
title | 2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one |
title_full | 2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one |
title_fullStr | 2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one |
title_full_unstemmed | 2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one |
title_short | 2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one |
title_sort | 2-tosyl-2,3,3a,4,9,9a-hexahydro-1h-benzo[f]isoindol-1-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685075/ https://www.ncbi.nlm.nih.gov/pubmed/23795094 http://dx.doi.org/10.1107/S1600536813011045 |
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