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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (2): 283-287. 上一篇    下一篇

研究论文

二氟亚甲基取代的Goniodiol类似物的合成

谢阳芬a，徐修华b，乐旭义b，游正伟b，卿凤翎*,a,b   

  1. (a东华大学化学化工与生物工程学院 上海 201620)
    (b中国科学院上海有机化学研究所有机氟化学重点实验室 上海 200032)
  • 收稿日期:2007-11-27 修回日期:2008-01-14 发布日期:2008-02-01
  • 通讯作者: 卿凤翎

Synthesis of gem-Difluoromethylenated Goniodiol

XIE Yang-Fenga,XU Xiu-Huab,YUE Xu-Yib
YOU Zheng-Weib,QING Feng-Ling*,a,b   

  1. (a College of Chemistry, Chemical Engineering and Biotechnology, Donghua Univer-sity, Shanghai 201620)
    (b Key Laboratory of Organofluorine Chemistry, Shanghai In-stitute of Organic Chemistry,
    Chinese Academy of Sciences, Shanghai 200032)
  • Received:2007-11-27 Revised:2008-01-14 Published:2008-02-01
  • Contact: QING Feng-Ling

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865

被引次数

6

合成了具有潜在生物活性的二氟亚甲基取代的Goniodiol类似物. 该合成路线的关键步骤为: 铟粉引发对醛的二氟炔丙基化反应引入二氟亚甲基; 在2,2,6,6-四甲基-1-氧基哌啶(TEMPO)催化下, 三氯异氰尿酸(TCCA)氧化1,5-二醇高效率地关环生成α,β-不饱和-δ-内脂环.

关键词: goniodiol, 苯乙烯内酯, α,β-不饱和-δ-内脂环, 二氟亚甲基取代物

An efficient and general route to gem-difluoromethylenated goniodiol has been developed. The in-troduction of a gem-difluoromethylene group was achieved by indium-mediated difluoropropargylation of aldehyde. The α,β-unsaturated-δ-lactone was successfully formed by the oxidation of 1,5-diols in the presence of catalytic 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and excess trichloroisocyanuric acid (TCCA).

Key words: styryllactone, goniodiol, α,β-unsaturated-δ-lactone, gem-difluoromethylenated compounds