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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...

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Detalles Bibliográficos
Autores principales: Fu, Jian-Hua, Wang, Zhao-Yang, Xue, Fu-Ling, Huo, Jing-Pei
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
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.
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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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