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.(-)-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,1HNMR,13CNMR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。
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.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2009年第7期1082-1091,共10页
Chinese Journal of Organic Chemistry
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
