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TBAB相转移催化合成7-烷氧基香豆素

Catalytic Synthesis of 7-Alkoxylcoumarins by TBAB

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【作者】 章维华蒋木庚

【Author】 ZHANG Wei-hua1,2, JIANG Mu-geng1 (1. College of Science, Nanjing Agricultural University, Nnajing 210095, China; 2. Research and Development Center of Fine Chemicals, Guizhou University, Guiyang 550025, China)

【机构】 南京农业大学理学院

【摘要】 以四正丁基溴化铵(TBAB)作相转移催化剂,7-羟基香豆素(1)或7-羟基-4-甲基香豆素(2)与5种卤代烃经Williamson反应合成了10个新的7-烷氧基香豆素,其结构经1H NMR,IR和MS表征。Williamson反应的优化条件为:以丙酮为溶剂,在碘化钾存在下,1或25mmol,n(1或2)∶n(卤代烃)∶n(碳酸钾)∶n(TBAB)=1.0∶1.5∶2.5∶0.1,于60℃~100℃反应5h~8h,产率84%~96%。

【Abstract】 Ten novel 7-alkoxylcoumarins were synthesized by Williamson reaction of 7-hydroxycoumarin(1) or 7-hydroxy-4-methylcoumarin(2) and five alkyl halides using tetrabutylammonium bromide(TBAB) as a phase transfer catalyst. The structures were characterized by 1H NMR, IR and MS. Optimum conditions of Williamson reaction in acetone in presence of KI at 60 ℃~80 ℃ for 5 h~8 h were as follows: 1(or 2) was 5 mmol; n(1 or 2) ∶n(alkyl halide) ∶n(K2CO3) ∶n(TBAB)=1.0 ∶1.5 ∶2.5 ∶0.1. The yields were 84%~96% under the optimum conditions.

【基金】 国家自然科学基金资助项目(20502011);教育部重点实验室绿色农药实验室开放基金资助项目(2007GDGP0101)
  • 【文献出处】 合成化学 ,Chinese Journal of Synthetic Chemistry , 编辑部邮箱 ,2008年05期
  • 【分类号】O643.32
  • 【被引频次】11
  • 【下载频次】378
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