7-去甲基青藤碱的选择性还原

IF 3.1 4区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemical Research in Chinese Universities Pub Date : 2008-09-01 DOI:10.1016/S1005-9040(08)60117-8

Yu-feng LI , Qing-min BU , Yi QIAN , Yi PAN , Jian-xin LI , Le-qun HUANG , Hong-jun ZHU

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引用次数: 1

摘要

筛选了几种硼氢化试剂:硼氢化钠、氰硼氢化钠、乙酰氧基硼氢化钠和三乙酰氧基硼氢化钠，分别用于还原青铜碱衍生的α、β-二羰基化合物7-去甲基青铜碱。采用三溴氢化钠或NaBH(OAc)3均可获得高度的区域选择性和立体选择性。经核磁共振、x -射线晶体衍射分析，证实产物为7R构型。并对选择性还原的机理进行了初步探讨。

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Selective Reduction of 7-Demethylsinomenine

Several borohydride reagents: sodium borohydride, sodium cyanoborohydride, soudium acetoxyborohydride and soudium triacetoxyborohydride were screened, respectively, for the reduction of 7-demethylsinomenine, which was an α,β-dicarbonyl compound derived from sinomenine. Highly regio- and stereo-selectivity was acquired when sodium cyanoborohydride or NaBH(OAc)₃ was used. The product was structurally confirmed as 7R configuration by NMR, X-ray crystal diffraction analysis. Some preliminary discussion was also made on the mechanism of the selective reduction.

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来源期刊

Chemical Research in Chinese Universities 化学-化学综合

CiteScore

5.30

自引率

6.50%

发文量

152

审稿时长

3.0 months

期刊介绍： The journal publishes research articles, letters/communications and reviews written by faculty members, researchers and postgraduates in universities, colleges and research institutes all over China and overseas. It reports the latest and most creative results of important fundamental research in all aspects of chemistry and of developments with significant consequences across subdisciplines. Main research areas include (but are not limited to): Organic chemistry (synthesis, characterization, and application); Inorganic chemistry (bio-inorganic chemistry, inorganic material chemistry); Analytical chemistry (especially chemometrics and the application of instrumental analysis and spectroscopy); Physical chemistry (mechanisms, catalysis, thermodynamics and dynamics); Polymer chemistry and polymer physics (mechanisms, material, catalysis, thermodynamics and dynamics); Quantum chemistry (quantum mechanical theory, quantum partition function, quantum statistical mechanics); Biochemistry; Biochemical engineering; Medicinal chemistry; Nanoscience (nanochemistry, nanomaterials).