Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (07): 1092-1095. Previous Articles     Next Articles

Original Articles

新型手性N-烷基-3-蒎胺类化合物的合成及其抑菌活性的研究

杨益琴; 李艳苹; 王石发*; 谷 文   

  1. (南京林业大学化学工程学院 南京 210037)
  • 收稿日期:2008-10-07 修回日期:2009-01-20 出版日期:2009-07-22 发布日期:2009-07-22
  • 通讯作者: 王石发

Synthesis and Bacteriostatic Activity of New-Type Chiral N-Alkyl-3-pinanamine

Yang, Yiqin; Li, Yanping; Wang, Shifa*; Gu, Wen   

  1. (College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037)
  • Received:2008-10-07 Revised:2009-01-20 Online:2009-07-22 Published:2009-07-22
  • Contact: Wang, Shifa

A new series of (1S,2S,3S,5R)-N-alkyl-3-pinanamines were synthesized from (1S,5S)-(-)- α-pinene. (1S,2S,5R)-(-)-3-pinanone was obtainted from (-)-α-pinene by hydroboration and oxidation with pyridinium dichromate (PDC), and then it was reacted with alkylamines under catalysis of boron trifluoride-diethyl etherate to afford Schiff bases, which were further reduced with KBH4 or NaBH4 to get (1S,2S,3S,5R)-N-alkyl-3-pinanamines. The structures of (1S,2S,5R)-N-alkyl-3-pinanimines and (1S,2S,3S, 5R)-N-alkyl-3-pinanamines were determined by FT-IR, 1H NMR, 13C NMR and GC-MS techniques. Anti-bacterial and antifungal tests of the synthesized N-alkyl-3-pinanamines were also carried out and it has been observed that (1S,2S,3S,5R)-N-(n-heptyl)-3-pinanamine was a more potent bactericide and fungicide than others, which has good activities against bacteria and fungi.

Key words: bacteriostatic activity, (1S,2S,5R)-N-alkyl-3-pinanimine, (1S,2S,5R)-(-)-3-pin- anone, (1S,2S,3S,5R)-N-alkyl-3-pinanamine