(2R,3R)-2-[(4-Chloro­phen­yl)hydroxy­meth­yl]cyclo­penta­none

The title compound, C(12)H(13)ClO(2), was prepared by the direct asymmetric inter­molecular aldol reaction of cyclo­penta­none and 4-chloro­benzaldehyde catalysed by l-tryptophan in water. The absolute mol­ecular structure was determined to be a racemic twin with 91% (2R,3R) isomer and 9% of the (2S...

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Detalles Bibliográficos
Autores principales: Deng, Dongsheng, Liu, Ping, Fu, Weijun, Ji, Baoming
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968076/
https://www.ncbi.nlm.nih.gov/pubmed/21581621
http://dx.doi.org/10.1107/S160053680804261X
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author Deng, Dongsheng
Liu, Ping
Fu, Weijun
Ji, Baoming
author_facet Deng, Dongsheng
Liu, Ping
Fu, Weijun
Ji, Baoming
author_sort Deng, Dongsheng
collection PubMed
description The title compound, C(12)H(13)ClO(2), was prepared by the direct asymmetric inter­molecular aldol reaction of cyclo­penta­none and 4-chloro­benzaldehyde catalysed by l-tryptophan in water. The absolute mol­ecular structure was determined to be a racemic twin with 91% (2R,3R) isomer and 9% of the (2S,3S) form. In the crystal structure, the mol­ecules are connected into a one-dimensional chain along the a axis through the formation of inter­molecular O—H⋯O hydrogen bonds. Further, non-conventional C—H⋯O and C—H⋯π contacts are observed in the structure, which consolidate the crystal packing.
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spelling pubmed-29680762010-12-30 (2R,3R)-2-[(4-Chloro­phen­yl)hydroxy­meth­yl]cyclo­penta­none Deng, Dongsheng Liu, Ping Fu, Weijun Ji, Baoming Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(12)H(13)ClO(2), was prepared by the direct asymmetric inter­molecular aldol reaction of cyclo­penta­none and 4-chloro­benzaldehyde catalysed by l-tryptophan in water. The absolute mol­ecular structure was determined to be a racemic twin with 91% (2R,3R) isomer and 9% of the (2S,3S) form. In the crystal structure, the mol­ecules are connected into a one-dimensional chain along the a axis through the formation of inter­molecular O—H⋯O hydrogen bonds. Further, non-conventional C—H⋯O and C—H⋯π contacts are observed in the structure, which consolidate the crystal packing. International Union of Crystallography 2008-12-20 /pmc/articles/PMC2968076/ /pubmed/21581621 http://dx.doi.org/10.1107/S160053680804261X Text en © Deng 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
Deng, Dongsheng
Liu, Ping
Fu, Weijun
Ji, Baoming
(2R,3R)-2-[(4-Chloro­phen­yl)hydroxy­meth­yl]cyclo­penta­none
title (2R,3R)-2-[(4-Chloro­phen­yl)hydroxy­meth­yl]cyclo­penta­none
title_full (2R,3R)-2-[(4-Chloro­phen­yl)hydroxy­meth­yl]cyclo­penta­none
title_fullStr (2R,3R)-2-[(4-Chloro­phen­yl)hydroxy­meth­yl]cyclo­penta­none
title_full_unstemmed (2R,3R)-2-[(4-Chloro­phen­yl)hydroxy­meth­yl]cyclo­penta­none
title_short (2R,3R)-2-[(4-Chloro­phen­yl)hydroxy­meth­yl]cyclo­penta­none
title_sort (2r,3r)-2-[(4-chloro­phen­yl)hydroxy­meth­yl]cyclo­penta­none
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968076/
https://www.ncbi.nlm.nih.gov/pubmed/21581621
http://dx.doi.org/10.1107/S160053680804261X
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AT liuping 2r3r24chlorophenylhydroxymethylcyclopentanone
AT fuweijun 2r3r24chlorophenylhydroxymethylcyclopentanone
AT jibaoming 2r3r24chlorophenylhydroxymethylcyclopentanone

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