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(3S,4R,4aS,7aR,12bS)-3-Cyclo­propyl­meth­yl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro­acetate methanol solvate

In the title compound, C(21)H(26)F(3)NO(6) (+)·CF(3)COO(−)·CH(3)OH or S-MNTX·CF(3)COO(−)·CH(3)OH (MNTX = methyl­naltrexone), the conformation of the polycyclic backbone of the noroxy­morphone skeleton can be simplified in terms of the angles between the least-squares planes of these rings. The dihed...

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Detalles Bibliográficos
Autores principales: Cai, Xu, Zhou, Xinbo, Zheng, Zhibing, Zhong, Wu, Li, Song
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009338/
https://www.ncbi.nlm.nih.gov/pubmed/21589050
http://dx.doi.org/10.1107/S1600536810041164
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author Cai, Xu
Zhou, Xinbo
Zheng, Zhibing
Zhong, Wu
Li, Song
author_facet Cai, Xu
Zhou, Xinbo
Zheng, Zhibing
Zhong, Wu
Li, Song
author_sort Cai, Xu
collection PubMed
description In the title compound, C(21)H(26)F(3)NO(6) (+)·CF(3)COO(−)·CH(3)OH or S-MNTX·CF(3)COO(−)·CH(3)OH (MNTX = methyl­naltrexone), the conformation of the polycyclic backbone of the noroxy­morphone skeleton can be simplified in terms of the angles between the least-squares planes of these rings. The dihedral angle between the cyclohexene and piperidine rings is 84.5 (6)°, while the dihedral angles between the planes of cyclohexane ring and the benzene, cyclohexene and piperidine rings, respectively, are 85.8 (6),80.0  (7) and 10.3 (7)°. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds. The trifluoro­acetate F atoms are disordered in a 0.710 (14):0.710 (14) ratio. The absolute stereochemistry was inferred from the use of (4R,4aS,7aR,12bS)-3-(cyclo­propyl­meth­yl)-4a,9-dihy­droxy-2,3,4,4a,5,6-hexa­hydro-1H-4,12-meth­ano­benzofuro[3,2-e]isoquinolin-7(7aH)-one as one of the starting materials.
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spelling pubmed-30093382010-12-30 (3S,4R,4aS,7aR,12bS)-3-Cyclo­propyl­meth­yl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro­acetate methanol solvate Cai, Xu Zhou, Xinbo Zheng, Zhibing Zhong, Wu Li, Song Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(21)H(26)F(3)NO(6) (+)·CF(3)COO(−)·CH(3)OH or S-MNTX·CF(3)COO(−)·CH(3)OH (MNTX = methyl­naltrexone), the conformation of the polycyclic backbone of the noroxy­morphone skeleton can be simplified in terms of the angles between the least-squares planes of these rings. The dihedral angle between the cyclohexene and piperidine rings is 84.5 (6)°, while the dihedral angles between the planes of cyclohexane ring and the benzene, cyclohexene and piperidine rings, respectively, are 85.8 (6),80.0  (7) and 10.3 (7)°. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds. The trifluoro­acetate F atoms are disordered in a 0.710 (14):0.710 (14) ratio. The absolute stereochemistry was inferred from the use of (4R,4aS,7aR,12bS)-3-(cyclo­propyl­meth­yl)-4a,9-dihy­droxy-2,3,4,4a,5,6-hexa­hydro-1H-4,12-meth­ano­benzofuro[3,2-e]isoquinolin-7(7aH)-one as one of the starting materials. International Union of Crystallography 2010-10-20 /pmc/articles/PMC3009338/ /pubmed/21589050 http://dx.doi.org/10.1107/S1600536810041164 Text en © Cai 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
Cai, Xu
Zhou, Xinbo
Zheng, Zhibing
Zhong, Wu
Li, Song
(3S,4R,4aS,7aR,12bS)-3-Cyclo­propyl­meth­yl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro­acetate methanol solvate
title (3S,4R,4aS,7aR,12bS)-3-Cyclo­propyl­meth­yl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro­acetate methanol solvate
title_full (3S,4R,4aS,7aR,12bS)-3-Cyclo­propyl­meth­yl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro­acetate methanol solvate
title_fullStr (3S,4R,4aS,7aR,12bS)-3-Cyclo­propyl­meth­yl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro­acetate methanol solvate
title_full_unstemmed (3S,4R,4aS,7aR,12bS)-3-Cyclo­propyl­meth­yl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro­acetate methanol solvate
title_short (3S,4R,4aS,7aR,12bS)-3-Cyclo­propyl­meth­yl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro­acetate methanol solvate
title_sort (3s,4r,4as,7ar,12bs)-3-cyclo­propyl­meth­yl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1h-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro­acetate methanol solvate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009338/
https://www.ncbi.nlm.nih.gov/pubmed/21589050
http://dx.doi.org/10.1107/S1600536810041164
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