有机化学 ›› 2014, Vol. 34 ›› Issue (5): 1010-1014.DOI: 10.6023/cjoc201311009 上一篇    下一篇

研究简报

五环[5.4.0.02,6.03,10.05,9]十一烷-内-8-醇的合成新方法

史胜斌a,b, 范桂娟b, 杨世源a, 李金山b, 廖龙渝b   

  1. a 西南科技大学 四川省非金属复合与功能材料重点实验室 绵阳 621010;
    b 中国工程物理研究院化工材料研究所 绵阳 621900
  • 收稿日期:2013-11-07 修回日期:2013-12-24 发布日期:2014-01-16
  • 通讯作者: 杨世源 E-mail:syyang@swust.edu.cn
  • 基金资助:

    国家重大基础研究(No. 00401010201)资助项目.

A Novel Synthetic Method of Endo-pentacyclo[5.4.0.02,6.03,10.05,9]- undecane-8-ol

Shi Shengbina,b, Fan Guijuanb, Yang Shiyuana, Li Jinshanb, Liao Longyub   

  1. a State Key Laboratory Cultivation Base for Nonmetal Composite and Functional Materials, Southwest University of Science and Technology, Mianyang 621010;
    b Institute of Chemical Materials, China Academy of Engineering Physics, Mianyang 621900
  • Received:2013-11-07 Revised:2013-12-24 Published:2014-01-16
  • Supported by:

    Project supported by the National Key Basic Research Grant Foundation (No. 00401010201).

五环[5.4.0.02,6.03,10.05,9]十一烷-内-8-醇是合成抗流感病毒医药、抗发炎药物、高能量燃料和燃料添加剂的关键中间体,本研究以环戊二烯和对苯醌为起始原料,经过Diels-Alder、光环化、羰基保护、氢化铝锂还原、水解、黄鸣龙还原等6步反应合成五环[5.4.0.02,6.03,10.05,9]十一烷-内-8-醇,总产率达44.9%. 本方法操作简便,分离纯化容易,成本低廉,收率高,为五环[5.4.0.02,6.03,10.05,9]十一烷-内-8-醇的规模化合成奠定了基础.

关键词: 环戊二烯, 五环[5.4.0.02,6.03,10.05,9]十一烷-内-8-醇, 合成

Endo-pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8-ol (5) was a key intermediate in the research of anti-influenza viruses medicines, anti-inflammatory drugs, high energy fuels and fuel additives. The synthesis of endo-pentacyclo- [5.4.0.02,6.03,10.05,9]undecane-8-ol (5) was successfully achieved by a six steps route which was consisted of Diels-Alder, photo-cyclo addition, carbonyl protecting, lithium aluminium hydride reduction, hydrolysis and Huang-Minlon reduction. The total yield was 44.9%. This method has the advantages of facilely available starting materials, simply conducted procedures, relatively high yield and easy purification, and is more suitable for scale-up production.

Key words: cyclopentadiene, endo-pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8-ol, synthesis