1,4a-Dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative

In the search for cancer chemopreventive agents, we have studied the Diels–Alder reaction of trans-communic acid with tetra­cyano­ethyl­ene in the presence of SiO(2) as catalyst. The title cycloadduct, C(26)H(30)N(4)O(2), was obtained in 75% yield. The mol­ecules are arranged in pairs through O—H⋯O...

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Detalles Bibliográficos
Autores principales: Rejouani, Nezha, Auhmani, Aziz, Ait Itto, My Youssef, Benharref, Ahmed, Daran, Jean-Claude
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960367/
https://www.ncbi.nlm.nih.gov/pubmed/21201501
http://dx.doi.org/10.1107/S1600536808001086
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author Rejouani, Nezha
Auhmani, Aziz
Ait Itto, My Youssef
Benharref, Ahmed
Daran, Jean-Claude
author_facet Rejouani, Nezha
Auhmani, Aziz
Ait Itto, My Youssef
Benharref, Ahmed
Daran, Jean-Claude
author_sort Rejouani, Nezha
collection PubMed
description In the search for cancer chemopreventive agents, we have studied the Diels–Alder reaction of trans-communic acid with tetra­cyano­ethyl­ene in the presence of SiO(2) as catalyst. The title cycloadduct, C(26)H(30)N(4)O(2), was obtained in 75% yield. The mol­ecules are arranged in pairs through O—H⋯O hydrogen bonds, forming an R (2) (2)(8) ring motif. Both the fused cyclohexyl rings adopt a chair conformation, whereas the nonfused ring adopts a half-chair conformation.
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spelling pubmed-29603672010-12-30 1,4a-Dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative Rejouani, Nezha Auhmani, Aziz Ait Itto, My Youssef Benharref, Ahmed Daran, Jean-Claude Acta Crystallogr Sect E Struct Rep Online Organic Papers In the search for cancer chemopreventive agents, we have studied the Diels–Alder reaction of trans-communic acid with tetra­cyano­ethyl­ene in the presence of SiO(2) as catalyst. The title cycloadduct, C(26)H(30)N(4)O(2), was obtained in 75% yield. The mol­ecules are arranged in pairs through O—H⋯O hydrogen bonds, forming an R (2) (2)(8) ring motif. Both the fused cyclohexyl rings adopt a chair conformation, whereas the nonfused ring adopts a half-chair conformation. International Union of Crystallography 2008-01-18 /pmc/articles/PMC2960367/ /pubmed/21201501 http://dx.doi.org/10.1107/S1600536808001086 Text en © International Union of Crystallography 2008 http://journals.iucr.org/services/termsofuse.html This is an open-access article distributed under the terms described at http://journals.iucr.org/services/termsofuse.html.
spellingShingle Organic Papers
Rejouani, Nezha
Auhmani, Aziz
Ait Itto, My Youssef
Benharref, Ahmed
Daran, Jean-Claude
1,4a-Dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative
title 1,4a-Dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative
title_full 1,4a-Dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative
title_fullStr 1,4a-Dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative
title_full_unstemmed 1,4a-Dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative
title_short 1,4a-Dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative
title_sort 1,4a-dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960367/
https://www.ncbi.nlm.nih.gov/pubmed/21201501
http://dx.doi.org/10.1107/S1600536808001086
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