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Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (07): 1092-1095. Previous Articles Next Articles
Original Articles
杨益琴; 李艳苹; 王石发*; 谷 文
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Yang, Yiqin; Li, Yanping; Wang, Shifa*; Gu, Wen
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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
Yang, Yiqin; Li, Yanping; Wang, Shifa*; Gu, Wen. Synthesis and Bacteriostatic Activity of New-Type Chiral N-Alkyl-3-pinanamine[J]. Chin. J. Org. Chem., 2009, 29(07): 1092-1095.
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