(1S,2R,6R,7aS)-1,2,6-Trihy­droxy­hexa­hydro-1H-pyrrolizin-3-one

In the title compound, C(7)H(11)NO(4), prepared via a Morita–Baylis–Hillman adduct, the five-membered ring bearing three O atoms approximates to a twisted conformation, whereas the other ring is close to an envelope, with a C atom in the flap position. The dihedral angle between their mean planes (a...

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Detalles Bibliográficos
Autores principales: Oliveira, F. L., Freire, K. R. L., Aparicio, R., Coelho, F.
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/PMC3297312/
https://www.ncbi.nlm.nih.gov/pubmed/22412502
http://dx.doi.org/10.1107/S1600536812002292
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author Oliveira, F. L.
Freire, K. R. L.
Aparicio, R.
Coelho, F.
author_facet Oliveira, F. L.
Freire, K. R. L.
Aparicio, R.
Coelho, F.
author_sort Oliveira, F. L.
collection PubMed
description In the title compound, C(7)H(11)NO(4), prepared via a Morita–Baylis–Hillman adduct, the five-membered ring bearing three O atoms approximates to a twisted conformation, whereas the other ring is close to an envelope, with a C atom in the flap position. The dihedral angle between their mean planes (all atoms) is 23.11 (9)°. The new stereocenters are created in a trans-diaxial configuration. In the crystal, O—H⋯O and O—H⋯(O,O) hydrogen bonds link the mol­ecules, generating a three-dimensional network. A weak C—H⋯O inter­action also occurs.
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spelling pubmed-32973122012-03-12 (1S,2R,6R,7aS)-1,2,6-Trihy­droxy­hexa­hydro-1H-pyrrolizin-3-one Oliveira, F. L. Freire, K. R. L. Aparicio, R. Coelho, F. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(7)H(11)NO(4), prepared via a Morita–Baylis–Hillman adduct, the five-membered ring bearing three O atoms approximates to a twisted conformation, whereas the other ring is close to an envelope, with a C atom in the flap position. The dihedral angle between their mean planes (all atoms) is 23.11 (9)°. The new stereocenters are created in a trans-diaxial configuration. In the crystal, O—H⋯O and O—H⋯(O,O) hydrogen bonds link the mol­ecules, generating a three-dimensional network. A weak C—H⋯O inter­action also occurs. International Union of Crystallography 2012-02-04 /pmc/articles/PMC3297312/ /pubmed/22412502 http://dx.doi.org/10.1107/S1600536812002292 Text en © Oliveira 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
Oliveira, F. L.
Freire, K. R. L.
Aparicio, R.
Coelho, F.
(1S,2R,6R,7aS)-1,2,6-Trihy­droxy­hexa­hydro-1H-pyrrolizin-3-one
title (1S,2R,6R,7aS)-1,2,6-Trihy­droxy­hexa­hydro-1H-pyrrolizin-3-one
title_full (1S,2R,6R,7aS)-1,2,6-Trihy­droxy­hexa­hydro-1H-pyrrolizin-3-one
title_fullStr (1S,2R,6R,7aS)-1,2,6-Trihy­droxy­hexa­hydro-1H-pyrrolizin-3-one
title_full_unstemmed (1S,2R,6R,7aS)-1,2,6-Trihy­droxy­hexa­hydro-1H-pyrrolizin-3-one
title_short (1S,2R,6R,7aS)-1,2,6-Trihy­droxy­hexa­hydro-1H-pyrrolizin-3-one
title_sort (1s,2r,6r,7as)-1,2,6-trihy­droxy­hexa­hydro-1h-pyrrolizin-3-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3297312/
https://www.ncbi.nlm.nih.gov/pubmed/22412502
http://dx.doi.org/10.1107/S1600536812002292
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