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 ,
  • 万惠新 ,
  • 蒋静 ,
  • 胡延维 ,
  • 陈晓蓓 ,
  • 张士磊
展开
  • 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

  网络出版日期: 2016-04-20

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 Pengfei ,
  • Wan Huixin ,
  • Jiang Jing ,
  • Hu Yanwei ,
  • Chen Xiaobei ,
  • Zhang Shilei
Expand
  • 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 date: 2016-02-26

  Revised date: 2016-04-12

  Online 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).

摘要

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.

本文引用格式

钱彭飞 , 万惠新 , 蒋静 , 胡延维 , 陈晓蓓 , 张士磊 . 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[J]. 有机化学, 2016 , 36(8) : 1878 -1882 . DOI: 10.6023/cjoc201602028

Abstract

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.

参考文献

[1] Wurtz, A. Bull. Soc. Chim. Fr. 1872, 17, 436.
[2] Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
[3] Mahrwald, R. Chem. Rev. 1999, 99, 1095.
[4] Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929.
[5] Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65.
[6] Guillena, G.; Nájera, C.; Ramón, D. J. Tetrahedron: Asymmetry 2007, 18, 2249.
[7] Nathan, H. P.; McMurray, J. G.; Pullman, W. E. Int. J. Impots. Res. 2001, 13, 2.
[8] Wang, X. Natl. J. Androl. 2009, 15, 379 (in Chinese).
(王翔, 中华男科学杂志, 2009, 15, 379.)
[9] Takemoto, M.; Iwakiri, Y.; Suzuki, Y.; Tanaka, K. Tetrahedron Lett. 2004, 43, 8061.
[10] Liu, S.; Scotti, J. S.; Knzmin, S. A. J. Org. Chem. 2013, 78, 8645.

文章导航

/