8-甲基-顺-6-壬烯酰(3,4-二甲氧基)苄胺的合成

Synthesis of 8-methyl-Z-6-nonenvanillyl amide

以香草醛和6-溴己酸为起始原料,经过6步反应合成了辣椒素类似物8-甲基-顺-6-壬烯酰(3,4-二甲氧基)苄胺.一方面,先将香草醛羟基进行甲基保护后转化为肟,然后经金属法还原产生重要的中间体3,4-二甲氧基苄胺;另一方面,首先利用固相反应将6-溴己酸转化为三苯基膦盐,再经Wittig缩合反应制备8-甲基-顺-6-壬烯酸,最后将产物与3,4-二甲氧基苄胺反应合成目标产物.利用IR、NMR等结构表征,表明经该法成功合成了目标化合物.

An efficient synthesis of 8-methyl-Z-6-nonenvanillyl amide was accomplished with vanillin and cyclohexanone through six steps. The key features of the approach involve： （1） synthesis of vanilly; （2）the installation of amine group by reduction of hydrozine vanillin in the present of powder zinc; （3） the oxidation of cyclohexanone by H2O2, the bromidation with HBr and the Wittig condensation using （6-carboxyhexyl）（triphenyl）phosphonium bromide and iso-butanal; （4） the connection of the unsaturated carboxylic acid 6 with the amine 4 to compound the target product. IR and MR spectra were used to confirm the structures.