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以5-氯甲基水杨醛为原料分别与N,N-二甲基烯丙基胺、N-甲基二烯丙基胺和甲基丙烯酸二甲氨基乙酯3种不饱和叔胺反应,合成了含有碳碳双键的季铵盐,并对反应条件进行了优化。确定较佳的合成条件为:在二氯甲烷溶液中,反应物摩尔配比为n(Ⅰ)∶n(Ⅱa)=1∶1,反应温度为0℃,反应时间为10 h。在该条件下,合成的目标化合物产率均在90%以上。通过IR、1HNMR、13CNMR和MS(ESI)分析手段对含有碳碳双键的季铵盐结构进行了表征。采用牛津杯法对目标化合物抑菌活性进行测试,结果显示,3种不饱和季铵盐对金黄色葡萄球菌均具有较好的抑菌活性,而对大肠杆菌没有明显的抑菌活性。
The reaction of 5-chloromethyl salicylaldehyde with 3 kinds of unsaturated tertiary amines such as N, N-dimethylallylamine, N-methyldiallylamine and dimethylaminoethylmethacrylate , A quaternary ammonium salt containing carbon-carbon double bonds was synthesized and the reaction conditions were optimized. The optimum synthesis conditions were as follows: the molar ratio of n (Ⅰ): n (Ⅱa) = 1: 1, the reaction temperature 0 ℃ and the reaction time 10 h in dichloromethane solution. Under these conditions, the yield of synthesized target compounds are above 90%. The quaternary ammonium salt structure containing carbon-carbon double bonds was characterized by IR, 1HNMR, 13CNMR and MS (ESI). The antibacterial activities of the target compounds were tested by the Oxford cup method. The results showed that the three kinds of unsaturated quaternary ammonium salts had good antibacterial activities against Staphylococcus aureus and no obvious antibacterial activity against Escherichia coli.