3-Oxo-18α-olean-28,13β-olide

The title terpene, C(30)H(46)O(3), is a 28,13β-lactone of oleanolic acid prepared with bis­muth trifluoro­methane­sulfonate (OTf), Bi(OTf)(3)·xH(2)O. All rings are trans-fused. The X-ray study shows the inversion of the orientation of 18-H in the lactonization reaction. A quantum chemical ab-initio...

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Detalles Bibliográficos
Autores principales: Santos, R. C., Pinto, R. M. A., Matos Beja, A., Salvador, J. A. R., Paixão, J. A.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007419/
https://www.ncbi.nlm.nih.gov/pubmed/21588427
http://dx.doi.org/10.1107/S160053681002903X
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author Santos, R. C.
Pinto, R. M. A.
Matos Beja, A.
Salvador, J. A. R.
Paixão, J. A.
author_facet Santos, R. C.
Pinto, R. M. A.
Matos Beja, A.
Salvador, J. A. R.
Paixão, J. A.
author_sort Santos, R. C.
collection PubMed
description The title terpene, C(30)H(46)O(3), is a 28,13β-lactone of oleanolic acid prepared with bis­muth trifluoro­methane­sulfonate (OTf), Bi(OTf)(3)·xH(2)O. All rings are trans-fused. The X-ray study shows the inversion of the orientation of 18-H in the lactonization reaction. A quantum chemical ab-initio Roothaan Hartree–Fock calculation of the equilibrium geometry of the isolated mol­ecule gives values for bond lengths and valency angles in close agreement with experimental values. The calculation also reproduces the observed mol­ecular conformation, with puckering parameters that agree well with those determined from the crystallographic study.
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spelling pubmed-30074192010-12-30 3-Oxo-18α-olean-28,13β-olide Santos, R. C. Pinto, R. M. A. Matos Beja, A. Salvador, J. A. R. Paixão, J. A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title terpene, C(30)H(46)O(3), is a 28,13β-lactone of oleanolic acid prepared with bis­muth trifluoro­methane­sulfonate (OTf), Bi(OTf)(3)·xH(2)O. All rings are trans-fused. The X-ray study shows the inversion of the orientation of 18-H in the lactonization reaction. A quantum chemical ab-initio Roothaan Hartree–Fock calculation of the equilibrium geometry of the isolated mol­ecule gives values for bond lengths and valency angles in close agreement with experimental values. The calculation also reproduces the observed mol­ecular conformation, with puckering parameters that agree well with those determined from the crystallographic study. International Union of Crystallography 2010-07-31 /pmc/articles/PMC3007419/ /pubmed/21588427 http://dx.doi.org/10.1107/S160053681002903X Text en © Santos et al. 2010 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
Santos, R. C.
Pinto, R. M. A.
Matos Beja, A.
Salvador, J. A. R.
Paixão, J. A.
3-Oxo-18α-olean-28,13β-olide
title 3-Oxo-18α-olean-28,13β-olide
title_full 3-Oxo-18α-olean-28,13β-olide
title_fullStr 3-Oxo-18α-olean-28,13β-olide
title_full_unstemmed 3-Oxo-18α-olean-28,13β-olide
title_short 3-Oxo-18α-olean-28,13β-olide
title_sort 3-oxo-18α-olean-28,13β-olide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007419/
https://www.ncbi.nlm.nih.gov/pubmed/21588427
http://dx.doi.org/10.1107/S160053681002903X
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AT matosbejaa 3oxo18aolean2813bolide
AT salvadorjar 3oxo18aolean2813bolide
AT paixaoja 3oxo18aolean2813bolide

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