化学学报 ›› 1991, Vol. 49 ›› Issue (6): 593-599. 上一篇    下一篇

研究论文

碳苷研究 XXVII. 黑豆素非环类似物的合成

蔡孟深;边兆群;乔梁;王动   

  1. 北京医科大学有机化学教研室;北京医科大学分析计算中心
  • 发布日期:1991-06-15

Studies on C-glycosides XXVII. Synthesis of acyclic bayin analogues

CAI MENGSHEN;BIAN ZHAOQUN;QIAO LIANG;WANG DONG   

  • Published:1991-06-15

本文报道天然黄酮碳苷黑豆素非环类似物的合成, 以2,4-二羟基苯乙酮为原料, 经酚羟基的单苄基化、Claisen重排、醇醛缩合、I2/DMSO/浓度H2SO4关环五步反应得到黄酮; 用Claisen重排, 分别在黄酮环生成之前和生成之后引入8-位取代基侧链, 收率国产高。修饰8-位烯丙基侧链, 得到了六个黑豆素类似物, 共中8的7-位为游离羟基。

关键词: 紫外分光光度法, 黄酮, 反应机理, 黄酮类化合物, 硫酸, 质谱法, 碳13核磁共振谱法, 质子磁共振谱法, 糖苷, DMSO

Synthesis of acyclic bayin analogs was reported. The substituted flavones were obtained by starting from 2,4-dihydroxyacetophenone, after monobenzylation, Claisen rearrangement, Aldol condensation and I2/DMSO/H2SO4 cyclization. Claisen rearrangement was used to introduce the 8-substituted side chain before or after the formation of flavone ring with high yield. Allylic side chain was modified to give six bayin analogs in which compound I has a free 7-hydroxy group.

Key words: ULTRAVIOLET SPECTROPHOTOMETRY, FLAVONE, REACTION MECHANISM, FLAVONOID, SULFURIC ACID, MASS SPECTROGRAPHY, C13 NMR SPECTROMETRY, PROTON MAGNETIC RESONANCE SPECTROMETRY, GLYCOSIDE, DMSO

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