3β-Acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide

The title compound, C(32)H(49)ClO(4), was obtained along with nitrile and lactam products in the POCl(3)-catalysed Beckmann rearrangement from 3β-acet­oxy-12-hydroxyiminoolean-28-olic acid methyl ester. The mechanism of the transformation leading to the title compound remains unclear and requires fu...

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Detalles Bibliográficos
Autores principales: Froelich, Anna, Kowiel, Marcin, Bednarczyk-Cwynar, Barbara, Zaprutko, Lucjusz, Gzella, Andrzej K.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3051923/
https://www.ncbi.nlm.nih.gov/pubmed/21522426
http://dx.doi.org/10.1107/S160053681100585X
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author Froelich, Anna
Kowiel, Marcin
Bednarczyk-Cwynar, Barbara
Zaprutko, Lucjusz
Gzella, Andrzej K.
author_facet Froelich, Anna
Kowiel, Marcin
Bednarczyk-Cwynar, Barbara
Zaprutko, Lucjusz
Gzella, Andrzej K.
author_sort Froelich, Anna
collection PubMed
description The title compound, C(32)H(49)ClO(4), was obtained along with nitrile and lactam products in the POCl(3)-catalysed Beckmann rearrangement from 3β-acet­oxy-12-hydroxyiminoolean-28-olic acid methyl ester. The mechanism of the transformation leading to the title compound remains unclear and requires further investigation. Rings A, B and E are in chair conformations, ring C has a twisted-boat conformation, ring D a conformation halfway between boat and twisted-boat and rings D and E are cis-fused. In the crystal, mol­ecules are connected by weak inter­molecular C—H⋯O hydrogen bonds into layers extending parallel to the bc plane.
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spelling pubmed-30519232011-04-26 3β-Acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide Froelich, Anna Kowiel, Marcin Bednarczyk-Cwynar, Barbara Zaprutko, Lucjusz Gzella, Andrzej K. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(32)H(49)ClO(4), was obtained along with nitrile and lactam products in the POCl(3)-catalysed Beckmann rearrangement from 3β-acet­oxy-12-hydroxyiminoolean-28-olic acid methyl ester. The mechanism of the transformation leading to the title compound remains unclear and requires further investigation. Rings A, B and E are in chair conformations, ring C has a twisted-boat conformation, ring D a conformation halfway between boat and twisted-boat and rings D and E are cis-fused. In the crystal, mol­ecules are connected by weak inter­molecular C—H⋯O hydrogen bonds into layers extending parallel to the bc plane. International Union of Crystallography 2011-02-23 /pmc/articles/PMC3051923/ /pubmed/21522426 http://dx.doi.org/10.1107/S160053681100585X Text en © Froelich 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
Froelich, Anna
Kowiel, Marcin
Bednarczyk-Cwynar, Barbara
Zaprutko, Lucjusz
Gzella, Andrzej K.
3β-Acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide
title 3β-Acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide
title_full 3β-Acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide
title_fullStr 3β-Acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide
title_full_unstemmed 3β-Acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide
title_short 3β-Acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide
title_sort 3β-acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3051923/
https://www.ncbi.nlm.nih.gov/pubmed/21522426
http://dx.doi.org/10.1107/S160053681100585X
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AT gzellaandrzejk 3bacetoxy12achlorodfriedooleanan2814bolide

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