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有机化学 ›› 2009, Vol. 29 ›› Issue (07): 1092-1095. 上一篇    下一篇

研究论文

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 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 Published:2009-07-22
  • Contact: Wang, Shifa

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被引次数

9 | 6

以(1S,5S)-(－)-α-蒎烯为原料合成了系列新型(1S,2S,3S,5R)-N-烷基-3-蒎胺类化合物. (－)-α-蒎烯经硼氢化氧化、重铬酸吡啶盐(PDC)氧化得到(1S,2S,5R)-(－)-3-蒎酮; 在BF3•(C2H5)2O催化下(1S,2S,5R)-(－)-3-蒎酮与伯胺化合物反应生成Schiff碱, 再经KBH4或NaBH4还原得到(1S,2S,3S,5R)-N-烷基-3-蒎胺类化合物. 采用FT-IR, 1H NMR, 13C NMR和GC-MS等分析手段对合成所得(1S,2S,5R)-N-烷基-3-蒎烷亚胺和(1S,2S,3S,5R)-N-烷基-3-蒎胺类化合物的结构进行了表征. 考察了(1S,2S,3S,5R)-N-烷基-3-蒎胺类化合物对大肠杆菌(E. coli)、金黄色葡萄球菌(S. aureus)、枯草芽胞杆菌(B. subtilis)、荧光假单胞菌(P. fluorescens)、白色念珠菌(C. albicans)、黑曲霉(A. niger)和米根霉(R. oryzae)等细菌和真菌的抑菌和杀菌活性. 结果表明(1S,2S,3S,5R)-N-正庚基-3-蒎胺对真菌和细菌均表现出良好的杀菌和抑菌活性.

关键词: (1S,2S,3S,5R)-N-烷基-3-蒎胺, (1S,2S,5R)-N-烷基-3-蒎酮亚胺, (1S,2S,5R)-(－)-3-蒎酮, 抑菌活性

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