N-{4-Bromo-2-[(S)-menth­yloxy]-5-oxo-2,5-dihydro-3-fur­yl}-l-valine

The title compound, C(19)H(30)BrNO(5), was obtained via a tandem asymmetric Michael addition–elimination reaction of 3,4-dibromo-5-[(S)-l-menth­yloxy]furan-2(5H)-one and l-valine in the presence of potassium hydroxide. The mol­ecular structure contains an approximately planar (r.m.s. deviation = 0.0...

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Detalles Bibliográficos
Autores principales: Song, Xiu-Mei, Li, Zhao-Yang, Wang, Zhao-Yang, Fu, Jian-Hua
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977280/
https://www.ncbi.nlm.nih.gov/pubmed/21583539
http://dx.doi.org/10.1107/S1600536809026129
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author Song, Xiu-Mei
Li, Zhao-Yang
Wang, Zhao-Yang
Fu, Jian-Hua
author_facet Song, Xiu-Mei
Li, Zhao-Yang
Wang, Zhao-Yang
Fu, Jian-Hua
author_sort Song, Xiu-Mei
collection PubMed
description The title compound, C(19)H(30)BrNO(5), was obtained via a tandem asymmetric Michael addition–elimination reaction of 3,4-dibromo-5-[(S)-l-menth­yloxy]furan-2(5H)-one and l-valine in the presence of potassium hydroxide. The mol­ecular structure contains an approximately planar (r.m.s. deviation = 0.0204 Å) five-membered furan­one ring and a six-membered menth­yloxy ring adopting a chair conformation. The crystal packing is stabilized by inter­molecular O—H⋯O and N—H⋯O hydrogen bonding.
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spelling pubmed-29772802010-12-30 N-{4-Bromo-2-[(S)-menth­yloxy]-5-oxo-2,5-dihydro-3-fur­yl}-l-valine Song, Xiu-Mei Li, Zhao-Yang Wang, Zhao-Yang Fu, Jian-Hua Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(30)BrNO(5), was obtained via a tandem asymmetric Michael addition–elimination reaction of 3,4-dibromo-5-[(S)-l-menth­yloxy]furan-2(5H)-one and l-valine in the presence of potassium hydroxide. The mol­ecular structure contains an approximately planar (r.m.s. deviation = 0.0204 Å) five-membered furan­one ring and a six-membered menth­yloxy ring adopting a chair conformation. The crystal packing is stabilized by inter­molecular O—H⋯O and N—H⋯O hydrogen bonding. International Union of Crystallography 2009-07-11 /pmc/articles/PMC2977280/ /pubmed/21583539 http://dx.doi.org/10.1107/S1600536809026129 Text en © Song et al. 2009 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
Song, Xiu-Mei
Li, Zhao-Yang
Wang, Zhao-Yang
Fu, Jian-Hua
N-{4-Bromo-2-[(S)-menth­yloxy]-5-oxo-2,5-dihydro-3-fur­yl}-l-valine
title N-{4-Bromo-2-[(S)-menth­yloxy]-5-oxo-2,5-dihydro-3-fur­yl}-l-valine
title_full N-{4-Bromo-2-[(S)-menth­yloxy]-5-oxo-2,5-dihydro-3-fur­yl}-l-valine
title_fullStr N-{4-Bromo-2-[(S)-menth­yloxy]-5-oxo-2,5-dihydro-3-fur­yl}-l-valine
title_full_unstemmed N-{4-Bromo-2-[(S)-menth­yloxy]-5-oxo-2,5-dihydro-3-fur­yl}-l-valine
title_short N-{4-Bromo-2-[(S)-menth­yloxy]-5-oxo-2,5-dihydro-3-fur­yl}-l-valine
title_sort n-{4-bromo-2-[(s)-menth­yloxy]-5-oxo-2,5-dihydro-3-fur­yl}-l-valine
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977280/
https://www.ncbi.nlm.nih.gov/pubmed/21583539
http://dx.doi.org/10.1107/S1600536809026129
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