(2aR*,5S*,6aS*,8aS*,E)-Ethyl 5-hy­droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa­hydro-1H-penta­leno[1,6-bc]oxepine-4-carboxyl­ate

The title compound, C(17)H(24)O(5), featuring a 2-carbeth­oxy-3-oxepanone unit in its intra­molecularly O—H⋯O hydrogen-bonded enol form, was obtained via [(CF(3)CO(2))(2)Rh](2)-catal­ysed intra­molecular O—H bond insertion in the α-diazo-ω-hy­droxy-β-ketoester, ethyl 4-[(1S,3aS,6R,6aS)-6-hy­droxy-2,...

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Detalles Bibliográficos
Autores principales: Mehta, Goverdhan, Kumar, C. S. Ananda, Sen, Saikat
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588985/
https://www.ncbi.nlm.nih.gov/pubmed/23476221
http://dx.doi.org/10.1107/S1600536812046776
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author Mehta, Goverdhan
Kumar, C. S. Ananda
Sen, Saikat
author_facet Mehta, Goverdhan
Kumar, C. S. Ananda
Sen, Saikat
author_sort Mehta, Goverdhan
collection PubMed
description The title compound, C(17)H(24)O(5), featuring a 2-carbeth­oxy-3-oxepanone unit in its intra­molecularly O—H⋯O hydrogen-bonded enol form, was obtained via [(CF(3)CO(2))(2)Rh](2)-catal­ysed intra­molecular O—H bond insertion in the α-diazo-ω-hy­droxy-β-ketoester, ethyl 4-[(1S,3aS,6R,6aS)-6-hy­droxy-2,2,3a-trimethyl-3-oxo-octa­hydro­penta­len-1-yl]-2-diazo-3-oxobutano­ate. The seven-membered oxacyclic ring, thus constructed on a cis-fused diquinane platform, was found to adopt a distorted boat–sofa conformation.
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spelling pubmed-35889852013-03-08 (2aR*,5S*,6aS*,8aS*,E)-Ethyl 5-hy­droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa­hydro-1H-penta­leno[1,6-bc]oxepine-4-carboxyl­ate Mehta, Goverdhan Kumar, C. S. Ananda Sen, Saikat Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(17)H(24)O(5), featuring a 2-carbeth­oxy-3-oxepanone unit in its intra­molecularly O—H⋯O hydrogen-bonded enol form, was obtained via [(CF(3)CO(2))(2)Rh](2)-catal­ysed intra­molecular O—H bond insertion in the α-diazo-ω-hy­droxy-β-ketoester, ethyl 4-[(1S,3aS,6R,6aS)-6-hy­droxy-2,2,3a-trimethyl-3-oxo-octa­hydro­penta­len-1-yl]-2-diazo-3-oxobutano­ate. The seven-membered oxacyclic ring, thus constructed on a cis-fused diquinane platform, was found to adopt a distorted boat–sofa conformation. International Union of Crystallography 2012-11-24 /pmc/articles/PMC3588985/ /pubmed/23476221 http://dx.doi.org/10.1107/S1600536812046776 Text en © Mehta et al. 2012 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
Mehta, Goverdhan
Kumar, C. S. Ananda
Sen, Saikat
(2aR*,5S*,6aS*,8aS*,E)-Ethyl 5-hy­droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa­hydro-1H-penta­leno[1,6-bc]oxepine-4-carboxyl­ate
title (2aR*,5S*,6aS*,8aS*,E)-Ethyl 5-hy­droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa­hydro-1H-penta­leno[1,6-bc]oxepine-4-carboxyl­ate
title_full (2aR*,5S*,6aS*,8aS*,E)-Ethyl 5-hy­droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa­hydro-1H-penta­leno[1,6-bc]oxepine-4-carboxyl­ate
title_fullStr (2aR*,5S*,6aS*,8aS*,E)-Ethyl 5-hy­droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa­hydro-1H-penta­leno[1,6-bc]oxepine-4-carboxyl­ate
title_full_unstemmed (2aR*,5S*,6aS*,8aS*,E)-Ethyl 5-hy­droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa­hydro-1H-penta­leno[1,6-bc]oxepine-4-carboxyl­ate
title_short (2aR*,5S*,6aS*,8aS*,E)-Ethyl 5-hy­droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa­hydro-1H-penta­leno[1,6-bc]oxepine-4-carboxyl­ate
title_sort (2ar*,5s*,6as*,8as*,e)-ethyl 5-hy­droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa­hydro-1h-penta­leno[1,6-bc]oxepine-4-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588985/
https://www.ncbi.nlm.nih.gov/pubmed/23476221
http://dx.doi.org/10.1107/S1600536812046776
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AT kumarcsananda 2ar5s6as8aseethyl5hydroxy778atrimethyl8oxo22a66a788a8boctahydro1hpentaleno16bcoxepine4carboxylate
AT sensaikat 2ar5s6as8aseethyl5hydroxy778atrimethyl8oxo22a66a788a8boctahydro1hpentaleno16bcoxepine4carboxylate

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