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3β-Hy­droxy­lup-20(29)-en-28-yl 1H-imidazole-1-carboxyl­ate

The title triterpene, C(34)H(52)N(2)O(3), is a C-28 carbamate derivative of betulin prepared in a one-step reaction from the commercially available 1,1′-carbonyl­diimidazole (CDI). All rings are fused trans. The X-ray study shows the retention of the configuration of C-28 with respect to the known c...

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Detalles Bibliográficos
Autores principales: Santos, R. C., Matos Beja, A., Salvador, J. A. R., Paixão, J. A.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007052/
https://www.ncbi.nlm.nih.gov/pubmed/21588073
http://dx.doi.org/10.1107/S160053681002489X
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author Santos, R. C.
Matos Beja, A.
Salvador, J. A. R.
Paixão, J. A.
author_facet Santos, R. C.
Matos Beja, A.
Salvador, J. A. R.
Paixão, J. A.
author_sort Santos, R. C.
collection PubMed
description The title triterpene, C(34)H(52)N(2)O(3), is a C-28 carbamate derivative of betulin prepared in a one-step reaction from the commercially available 1,1′-carbonyl­diimidazole (CDI). All rings are fused trans. The X-ray study shows the retention of the configuration of C-28 with respect to the known chiral centres of the molecule. In the crystal, the mol­ecules are O—H⋯O hydrogen bonded via the hy­droxy group and the carbonyl group of the carbamate function into chains running along the c axis. A quantum-mechanical ab initio Roothaan Hartree–Fock calculation of the equilibrium geometry of the isolated mol­ecule gives values for bond-lengths and valency angles close to the experimental values. The calculations also reproduce the mol­ecular conformation well, with calculated puckering parameters that agree well with the observed values.
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spelling pubmed-30070522010-12-30 3β-Hy­droxy­lup-20(29)-en-28-yl 1H-imidazole-1-carboxyl­ate Santos, R. C. Matos Beja, A. Salvador, J. A. R. Paixão, J. A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title triterpene, C(34)H(52)N(2)O(3), is a C-28 carbamate derivative of betulin prepared in a one-step reaction from the commercially available 1,1′-carbonyl­diimidazole (CDI). All rings are fused trans. The X-ray study shows the retention of the configuration of C-28 with respect to the known chiral centres of the molecule. In the crystal, the mol­ecules are O—H⋯O hydrogen bonded via the hy­droxy group and the carbonyl group of the carbamate function into chains running along the c axis. A quantum-mechanical ab initio Roothaan Hartree–Fock calculation of the equilibrium geometry of the isolated mol­ecule gives values for bond-lengths and valency angles close to the experimental values. The calculations also reproduce the mol­ecular conformation well, with calculated puckering parameters that agree well with the observed values. International Union of Crystallography 2010-06-30 /pmc/articles/PMC3007052/ /pubmed/21588073 http://dx.doi.org/10.1107/S160053681002489X 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.
Matos Beja, A.
Salvador, J. A. R.
Paixão, J. A.
3β-Hy­droxy­lup-20(29)-en-28-yl 1H-imidazole-1-carboxyl­ate
title 3β-Hy­droxy­lup-20(29)-en-28-yl 1H-imidazole-1-carboxyl­ate
title_full 3β-Hy­droxy­lup-20(29)-en-28-yl 1H-imidazole-1-carboxyl­ate
title_fullStr 3β-Hy­droxy­lup-20(29)-en-28-yl 1H-imidazole-1-carboxyl­ate
title_full_unstemmed 3β-Hy­droxy­lup-20(29)-en-28-yl 1H-imidazole-1-carboxyl­ate
title_short 3β-Hy­droxy­lup-20(29)-en-28-yl 1H-imidazole-1-carboxyl­ate
title_sort 3β-hy­droxy­lup-20(29)-en-28-yl 1h-imidazole-1-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007052/
https://www.ncbi.nlm.nih.gov/pubmed/21588073
http://dx.doi.org/10.1107/S160053681002489X
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