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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...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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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. |
format | Text |
id | pubmed-3009338 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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