Nucleophilic Substitution in the Allylic System of Codeine and Pseudocodeine: Reactions with lithium cyano(methyl)-and (aryl)cyanocuprates. Crystal and molecular structure of 8?-phenyl-6,7-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan and 6?-phenyl-7,8-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan
Тип публикации: Journal Article
Дата публикации: 1994-02-09
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SJR: 0.491
CiteScore: 3
Impact factor: 1.8
ISSN: 0018019X, 15222675
Catalysis
Organic Chemistry
Drug Discovery
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
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Nucleophilic substitution of 6β-chloro-7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan (1) and 8α-bromo-6,7-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan (2) with lithium cyano(methyl)- and (aryl)cyanocuprates(I) (5a–c) was accompanied by allylic rearrangement with both change and retention of orientation of the substituting group (Scheme 1, Table 1). Nucleophilic substitution in 7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-yl methanesulfonate (3) and 7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6β-yl methanesulfonate (4) proceeded without allylic rearrangement with both change and retention of the orientation of the substituting group (Scheme 2, Table 1). X-Ray diffraction studies of the products 6,7-didehydro-4,5α-epoxy-3-methoxy-17-methyl-8α-phenylmorphinan (6b) and 7,8-didehydro-4,5α-epoxy-3-methoxy-17-methyl-6β-phenylmorphinan (7b) were carried out (Figs. 1 and 2).
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Kalinin V. N. et al. Nucleophilic Substitution in the Allylic System of Codeine and Pseudocodeine: Reactions with lithium cyano(methyl)-and (aryl)cyanocuprates. Crystal and molecular structure of 8?-phenyl-6,7-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan and 6?-phenyl-7,8-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan // Helvetica Chimica Acta. 1994. Vol. 77. No. 1. pp. 164-170.
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Kalinin V. N., Belyakova I. L., Derunov V. V., Petrovskii P. V., Yanovski A. I., Struchkov Y. T., Schmidhammer H., Park J. K. Nucleophilic Substitution in the Allylic System of Codeine and Pseudocodeine: Reactions with lithium cyano(methyl)-and (aryl)cyanocuprates. Crystal and molecular structure of 8?-phenyl-6,7-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan and 6?-phenyl-7,8-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan // Helvetica Chimica Acta. 1994. Vol. 77. No. 1. pp. 164-170.
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TY - JOUR
DO - 10.1002/hlca.19940770119
UR - https://doi.org/10.1002/hlca.19940770119
TI - Nucleophilic Substitution in the Allylic System of Codeine and Pseudocodeine: Reactions with lithium cyano(methyl)-and (aryl)cyanocuprates. Crystal and molecular structure of 8?-phenyl-6,7-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan and 6?-phenyl-7,8-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan
T2 - Helvetica Chimica Acta
AU - Kalinin, Valery N.
AU - Belyakova, Irina L
AU - Derunov, Vladimir V
AU - Petrovskii, Pavel V.
AU - Yanovski, Aleksandr I
AU - Struchkov, Yurii T
AU - Schmidhammer, Helmut
AU - Park, Jin K.
PY - 1994
DA - 1994/02/09
PB - Wiley
SP - 164-170
IS - 1
VL - 77
SN - 0018-019X
SN - 1522-2675
ER -
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@article{1994_Kalinin,
author = {Valery N. Kalinin and Irina L Belyakova and Vladimir V Derunov and Pavel V. Petrovskii and Aleksandr I Yanovski and Yurii T Struchkov and Helmut Schmidhammer and Jin K. Park},
title = {Nucleophilic Substitution in the Allylic System of Codeine and Pseudocodeine: Reactions with lithium cyano(methyl)-and (aryl)cyanocuprates. Crystal and molecular structure of 8?-phenyl-6,7-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan and 6?-phenyl-7,8-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan},
journal = {Helvetica Chimica Acta},
year = {1994},
volume = {77},
publisher = {Wiley},
month = {feb},
url = {https://doi.org/10.1002/hlca.19940770119},
number = {1},
pages = {164--170},
doi = {10.1002/hlca.19940770119}
}
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Kalinin, Valery N., et al. “Nucleophilic Substitution in the Allylic System of Codeine and Pseudocodeine: Reactions with lithium cyano(methyl)-and (aryl)cyanocuprates. Crystal and molecular structure of 8?-phenyl-6,7-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan and 6?-phenyl-7,8-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan.” Helvetica Chimica Acta, vol. 77, no. 1, Feb. 1994, pp. 164-170. https://doi.org/10.1002/hlca.19940770119.