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有机化学 ›› 2016, Vol. 36 ›› Issue (8): 1878-1882.DOI: 10.6023/cjoc201602028 上一篇    下一篇

研究论文

一类特殊的分子内类Aldol反应产物他达拉非有关物质E的合成研究

钱彭飞a, 万惠新b, 蒋静a, 胡延维a, 陈晓蓓c, 张士磊a   

  1. a 苏州大学药学院 苏州 215123;
    b 上海医药集团股份有限公司中央研究院 上海 201203;
    c 华东理工大学药学院 上海 200237
  • 收稿日期:2016-02-26 修回日期:2016-04-12 发布日期:2016-04-20
  • 通讯作者: 陈晓蓓, 张士磊 E-mail:xiaobei@ecust.edu.cn;zhangshilei@suda.edu.cn
  • 基金资助:

    国家自然科学基金（No. 21202112）、教育部博士点基金新教师类项目（20123201120019）、江苏高校优势学科建设工程资助项目.

Discovery of a Special Intramolecular Aldol-Like Reaction in the Synthesis of Related Substance E of Tadalafil

Qian Pengfeia, Wan Huixinb, Jiang Jinga, Hu Yanweia, Chen Xiaobeic, Zhang Shileia   

  1. a College of Pharmaceutical Science, Soochow University, Suzhou 215123;
    b Central Research Institute of Shanghai Pharmaceuticals Holding Co., Ltd., Shanghai 201203;
    c School of Pharmacy, East China University of Science & Technology, Shanghai 200237
  • Received:2016-02-26 Revised:2016-04-12 Published:2016-04-20
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Grant No.21202112), Ph.D. Programs Foundation of Ministry of Education of China (No. 20123201120019) and PAPD (A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions).

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在合成他达拉非有关物质D、E、G、H的过程中，发现了一类特殊的分子内类aldol反应. 在这个反应中，酮的α位碳进攻酰胺的羰基，形成一个稳定的胺基半缩酮结构. 这个反应需要用硅胶催化来实现，其它酸碱性反应条件均难以得到所需的产物. 这是对aldol反应一个有意义的补充和拓展.

关键词: aldol反应, 酰胺, 硅胶催化, 胺基半缩酮, 他达拉非有关物质

In the synthesis of related substance E of tadalafil, a special intramolecular aldol-like reaction was discovered. In this reaction, the α-carbon of ketone attacks the carbonyl group of amide, forming a stable amino hemiketal structure. This reaction can only be realized under the catalysis of silica gel, and other acidic or basic reaction conditions are difficult to obtain the desired product. This finding is a meaningful supplement and extension to aldol reactions.

Key words: aldol reaction, amide, catalysis on silica gel, amino hemiketal, related substances of tadalafil