香草酰胺化合物的合成

Synthesis of Vanillyl Amide

以价廉易得的香草醛为起始原料,经过3步反应,高产率合成了酚羟基由对甲苯磺酰基保护的香草胺类化合物5。将香草醛转化为香草肟4,用金属还原生成中间体香草胺;将6-溴己酸固相反应合成三苯基季膦盐再经Wittig缩合反应制备8-甲基-顺-6-壬烯酸,最后其与香草胺反应后,超声波促进酯水解合成目标产物1,总收率达47.93%。利用红外光谱、核磁共振谱和高分辨质谱等结构表征的结果表明,已成功合成了目标化合物。

An efficient and high-yield synthesis of 3-methoxy-4-formylphenonyl p-methylbensulphonate （5） was accomplished with vanillin as the starting material in three steps. It involved the converstion of vanillin into hydrazine（4） and the metalic reduction of hydrazine 4 into the intermediate vanillic amine. The phosphonium 6 was synthesized in solid phase by the reaction of 6-bromohexyoic acid with triphenyiphosphine, then the Wittig condensation of phosphonium 6 with iso-butanol afforded 8-methoxynon-cis-6-enoic acid（7）. Finally, compound 7 was connected with the amine 5, and then was hydrolyzed to the target compound under ultrasonic condition. IR, NMR and HRMS were used to confirm the structure of the title compound.