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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
  • 期刊名称:有机化学,2009,已录用,正在排版
  • 时间:0
  • 分类:TQ616.8[化学工程—精细化工] TQ246.31[化学工程—有机化工]
  • 作者机构:[1]南京林业大学化学工程学院,南京210037
  • 相关基金:国家自然科学基金(No.30571468)、国家自然科学基金重点(No.30430580)资助项目.
  • 相关项目:单萜烯烃合成新型手性胺类化合物反应的研究
中文摘要:

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.(-)-a-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.

英文摘要:

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.

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