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(5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one
The title compound, C(18)H(26)ClNO(3), was obtained via a tandem asymmetric Michael addition–elimination reaction of 3,4-dichloro-5-(S)-(l-menthyloxy)furan-2(5H)-one and 2,5-dihydro-1H-pyrrole in the presence of potassium fluoride. In the molecule, the nearly planar dihydropyrrole ring [maximum...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050327/ https://www.ncbi.nlm.nih.gov/pubmed/21522785 http://dx.doi.org/10.1107/S1600536810051226 |
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author | Fu, Jian-Hua Wang, Zhao-Yang Xue, Fu-Ling Huo, Jing-Pei |
author_facet | Fu, Jian-Hua Wang, Zhao-Yang Xue, Fu-Ling Huo, Jing-Pei |
author_sort | Fu, Jian-Hua |
collection | PubMed |
description | The title compound, C(18)H(26)ClNO(3), was obtained via a tandem asymmetric Michael addition–elimination reaction of 3,4-dichloro-5-(S)-(l-menthyloxy)furan-2(5H)-one and 2,5-dihydro-1H-pyrrole in the presence of potassium fluoride. In the molecule, the nearly planar dihydropyrrole ring [maximum atomic deviation = 0.019 (3) Å] is oriented at a dihedral angle of 10.73 (8)° to the the nearly planar furanone ring [maximum atomic deviation = 0.011 (2) Å]; the cyclohexane ring adopts a chair conformation. In the crystal, molecules are linked via weak intermolecular C—H⋯O hydrogen bonds, forming supramolecular chains running along the b axis. |
format | Text |
id | pubmed-3050327 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-30503272011-04-26 (5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one Fu, Jian-Hua Wang, Zhao-Yang Xue, Fu-Ling Huo, Jing-Pei Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(26)ClNO(3), was obtained via a tandem asymmetric Michael addition–elimination reaction of 3,4-dichloro-5-(S)-(l-menthyloxy)furan-2(5H)-one and 2,5-dihydro-1H-pyrrole in the presence of potassium fluoride. In the molecule, the nearly planar dihydropyrrole ring [maximum atomic deviation = 0.019 (3) Å] is oriented at a dihedral angle of 10.73 (8)° to the the nearly planar furanone ring [maximum atomic deviation = 0.011 (2) Å]; the cyclohexane ring adopts a chair conformation. In the crystal, molecules are linked via weak intermolecular C—H⋯O hydrogen bonds, forming supramolecular chains running along the b axis. International Union of Crystallography 2010-12-11 /pmc/articles/PMC3050327/ /pubmed/21522785 http://dx.doi.org/10.1107/S1600536810051226 Text en © Fu et al. 2011 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 Fu, Jian-Hua Wang, Zhao-Yang Xue, Fu-Ling Huo, Jing-Pei (5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one |
title | (5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one |
title_full | (5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one |
title_fullStr | (5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one |
title_full_unstemmed | (5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one |
title_short | (5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one |
title_sort | (5s)-3-chloro-4-(2,5-dihydro-1h-pyrrol-1-yl)-5-[(1r,2s,5r)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5h)-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050327/ https://www.ncbi.nlm.nih.gov/pubmed/21522785 http://dx.doi.org/10.1107/S1600536810051226 |
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