(1S,2R,4S)-1-[(Benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol

The title compound, C(17)H(25)NO(2), was synthesized by epoxidation of the double bond of (S)-perillyl alcohol [(S)-4-isopropenyl-1-cyclo­hexenyl­methanol], followed by the oxirane ring-opening by benzyl­amine using [Ca(CF(3)CO(2))(2)] as catalyst under solvent-free condition at 313 K. The mol­ecula...

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Autores principales: Outouch, Rachid, Boualy, Brahim, Ali, Mustapha Ait, Firdoussi, Larbi El, Rizzoli, Corrado
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050382/
https://www.ncbi.nlm.nih.gov/pubmed/21522697
http://dx.doi.org/10.1107/S1600536810052323
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author Outouch, Rachid
Boualy, Brahim
Ali, Mustapha Ait
Firdoussi, Larbi El
Rizzoli, Corrado
author_facet Outouch, Rachid
Boualy, Brahim
Ali, Mustapha Ait
Firdoussi, Larbi El
Rizzoli, Corrado
author_sort Outouch, Rachid
collection PubMed
description The title compound, C(17)H(25)NO(2), was synthesized by epoxidation of the double bond of (S)-perillyl alcohol [(S)-4-isopropenyl-1-cyclo­hexenyl­methanol], followed by the oxirane ring-opening by benzyl­amine using [Ca(CF(3)CO(2))(2)] as catalyst under solvent-free condition at 313 K. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O hydrogen bonds, forming chains parallel to the a axis, which are further connected by O—H⋯O hydrogen bonds into sheets parallel to (010). The absolute configuration of the mol­ecule is known from the synthetic procedure.
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spelling pubmed-30503822011-04-26 (1S,2R,4S)-1-[(Benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol Outouch, Rachid Boualy, Brahim Ali, Mustapha Ait Firdoussi, Larbi El Rizzoli, Corrado Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(17)H(25)NO(2), was synthesized by epoxidation of the double bond of (S)-perillyl alcohol [(S)-4-isopropenyl-1-cyclo­hexenyl­methanol], followed by the oxirane ring-opening by benzyl­amine using [Ca(CF(3)CO(2))(2)] as catalyst under solvent-free condition at 313 K. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O hydrogen bonds, forming chains parallel to the a axis, which are further connected by O—H⋯O hydrogen bonds into sheets parallel to (010). The absolute configuration of the mol­ecule is known from the synthetic procedure. International Union of Crystallography 2010-12-18 /pmc/articles/PMC3050382/ /pubmed/21522697 http://dx.doi.org/10.1107/S1600536810052323 Text en © Outouch 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
Outouch, Rachid
Boualy, Brahim
Ali, Mustapha Ait
Firdoussi, Larbi El
Rizzoli, Corrado
(1S,2R,4S)-1-[(Benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol
title (1S,2R,4S)-1-[(Benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol
title_full (1S,2R,4S)-1-[(Benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol
title_fullStr (1S,2R,4S)-1-[(Benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol
title_full_unstemmed (1S,2R,4S)-1-[(Benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol
title_short (1S,2R,4S)-1-[(Benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol
title_sort (1s,2r,4s)-1-[(benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050382/
https://www.ncbi.nlm.nih.gov/pubmed/21522697
http://dx.doi.org/10.1107/S1600536810052323
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