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(9S,13R,14R)-7,8-二脱氢-3,4,7-三甲氧基-17-甲基吗啡喃-6-酮

(9S,13R,14R)-7,8-Didehydro-3,4,7-trimeth-oxy-17-methyl-morphinan-6-one.

作者信息

Li Yu-Feng, Qian Yi, Yin Li-He, Lv Ran, Zhu Hong-Jun

机构信息

Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China.

出版信息

Acta Crystallogr Sect E Struct Rep Online. 2009 Mar 6;65(Pt 4):o689. doi: 10.1107/S1600536808040749.

DOI:10.1107/S1600536808040749
PMID:21582431
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2969083/
Abstract

The title compound, C(20)H(25)NO(4), was synthesized by a Mitsunobu reaction of sinomenine [(9S,13R,14R)-7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one] with methanol. The chiral centers were unchanged during the reaction. Intra-molecular C-H⋯O hydrogen bonds result in the formation of six-membered rings.

摘要

标题化合物C(20)H(25)NO(4)是通过青藤碱[(9S,13R,14R)-7,8-二脱氢-4-羟基-3,7-二甲氧基-17-甲基吗啡喃-6-酮]与甲醇的 Mitsunobu 反应合成的。反应过程中手性中心未发生变化。分子内C-H⋯O氢键导致形成六元环。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d950/2969083/a4fd1e77262f/e-65-0o689-fig1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d950/2969083/a4fd1e77262f/e-65-0o689-fig1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d950/2969083/a4fd1e77262f/e-65-0o689-fig1.jpg

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本文引用的文献

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A short history of SHELX.SHELX简史。
Acta Crystallogr A. 2008 Jan;64(Pt 1):112-22. doi: 10.1107/S0108767307043930. Epub 2007 Dec 21.
(7R,8S,9S,12S)-1-Benz-yloxy-13,14-didehydro-12-hy-droxy-2,13-dimeth-oxy-N-methyl-morphinane.
(7R,8S,9S,12S)-1-苄氧基-13,14-二脱氢-12-羟基-2,13-二甲氧基-N-甲基吗啡烷
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4
(8S,9S,10R)-4-(4-Chloro-benz-yloxy)-7,8-didehydro-3,7-dimeth-oxy-17-methyl-morphinan-6-one monohydrate.（8S，9S，10R）-4-（4-氯苄氧基）-7，8-二脱氢-3，7-二甲氧基-17-甲基吗啡喃-6-酮一水合物
Acta Crystallogr Sect E Struct Rep Online. 2011 May 1;67(Pt 5):o1190. doi: 10.1107/S1600536811013973. Epub 2011 Apr 22.
5
(9S,13R,14S)-7,8-Didehydro-4-(4-iodo-benz-yloxy)-3,7-dimeth-oxy-17-methyl-morphinan-6-one monohydrate.（9S，13R，14S）-7，8-二脱氢-4-（4-碘苄氧基）-3，7-二甲氧基-17-甲基吗啡喃-6-酮一水合物
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