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贝母植物碱研究 ⅩⅢ.西贝素中仲醇羟基及羰基的位置和A,B环的立体化学

A STUDY OF FRITILLARIA ALKALOIDS XIII.THE CHEMISTRY OF SIPEIMINE (IMPERIALIN)THE LOCATION OF THE SECONDARY HYDROXYL AND THE CARBONYL GROUPS AND THE STEREOCHEMISTRY OF RINGS A AND B

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【作者】 刘铸晋陆仁荣何凤珍朱子清黄文魁

【Author】 LIU CHU-TSIN, LOH JEN-YUNG AND HO FUN-ZWUN(Institute of Organic Chemistry, Academia Sinica) andCHU TZE-TSIN AND HWANG WEN-KEUI(Department of Chemistry, Lanchow University)

【机构】 中国科学院有机化学研究所中国科学院有机化学研究所兰州大学化学系

【摘要】 从旋光数据及脱氧西贝酮的紫外光谱考虑,将西贝素的仲醇羟基定在C-3β-位.为便于解释脱水西贝素异常的化学及光谱性质,认为它具环丙基酮类型的结构,从而西贝素中的羰基应位于C-6.众多的旋光数据对这推断亦无矛盾.对西贝素中叔醇基的位置及其A,B两环的立体化学也有所讨论.西贝素的结构式经推定如(XIV)式.

【Abstract】 A survey of the molecular rotation data and an examination of the characteristics of the UV absorption spectrum of desoxosipeimone (desoxodihydroimperialon, Ⅱ), coupled with biogenetic considerations, appear to favour the location of the secondary hydroxyl group in sipeimine (imperialin) at C-3.The carbonyl group of sipeimine is tentatively assigned to C-6 in order to account for the unusual chemical and spectral properties of anhydrosipeimine (Ⅹ), which seems to behave like a cyclopropyl ketone. In the meantime, an extensive study of existing rotation data indicates that position-6 is equally acceptable as position-7 as the site of the carbonyl. The latter position has been favoured by Morgan and Barltrop.The location of the tertiary hydroxyl group and the stereochemistry of the rings A and B are discussed.The structure of sipeimine (imperialin) is provisionally presented as (XIV).

  • 【文献出处】 化学学报 ,Acta Chimica Sinica , 编辑部邮箱 ,1961年02期
  • 【被引频次】7
  • 【下载频次】78
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