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化学学报
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化学学报 ›› 1988, Vol. 46 ›› Issue (9): 887-894. 上一篇    下一篇

研究论文

碳苷研究 V: 用Grignard试剂合成取代苯酚中酚羟基的保护及脱保护

蔡孟深;曹小冬   

  1. 北京医科大学有机化学教研室
  • 发布日期:1988-09-15

Studies of C-glycosides V: Protection and deprotection of phenolic hydroxy group in the synthesis of substituted phenols by Grignard reagents

CAI MENGSHEN;CAO XIAODONG   

  • Published:1988-09-15

PDF

558

被引次数

11

本文报道了一些取代苯酚的合成, 并探讨了用Grignard试剂合成取代苯酚中酚羟基的保护及脱保护的问题. 利用苄基和甲基作为酚羟基的保护基, 对文献报道的切断醚键脱保护方法进行了评价. 找到了两种新体系能在更温和条件下切断醚键的方法, 指出了它们的适用条件. 实验结果符合硬软酸碱理论.

关键词: 苯酚 P, 甲基, 黄酮类化合物, 保护, 糖苷, 苄基, 葛根, 酸碱平衡, 格氏试剂

The synthesis of some substituted phenols using Grignard reagents were reported and the protection and the deprotection of phenolic hydroxy group were also investigated. Me and benzyl groups were used for the protection of phenols, and the reported methods of deprotection by BBr3, Me3SiI or AlCl3-EtSH were evaluated. Two new systems, AlCl3-EtSH-NaI and AlI3-EtSH, for the cleavage of there ether linkages under milder conditions were developed and a no. of protected phenolic ethers were cleaved readily at 0?or room temperature The experimental results were in accordance with HSAB theory.

Key words: PHENOL P, METHYL GROUP, FLAVONOID, CONSERVATION, GLYCOSIDE, BENZYL GROUP, PUERARIA LOBATA, ACID-BASE EQUILIBRIUM, GRIGNARD REAGENT

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