摘要
利用异佛尔酮为起始原料合成了一种消旋八氢香豆素衍生物,并初步评估了它的香气特征。认为它作为一种稠环内酯化合物具有用于日化香精的调配的潜在可能。以钯/碳为催化剂,异佛尔酮经选择性催化氢化得到二氢异佛尔酮;二氢异佛尔酮的烯胺与丙烯酸甲酯发生迈克尔加成反应得到的3-(2,4,4-三甲基-6-氧代-环己基)丙酸甲酯,再经碱性条件下水解,硼氢化钾还原得到δ-羟基羧酸,最后δ-羟基羧酸经酸催化发生分子内酯化反应生成一种消旋八氢香豆素衍生物5,7,7-三甲基-八氢-2H-苯并吡喃-2-酮。目标化合物通过红外光谱、核磁共振氢谱、碳谱以及质谱进行了表征。
A new racemic octahydrocoumarin derivative was synthesized from isophorone and its aroma characteristics were evaluated preliminarily.As a kind of fused-ring lactone compound,It could be used for the daily fragrances.Using palladium on carbon as catalyst,isophorone was reduced selectively to obtain dihydroisophorone;Methyl 3-(2,4,4-trimethyl-6-oxo-cyclohexyl)propanoate was obtained by Michael addition reaction of enamine of dihydroisophorone with methyl acrylate.It was then hydrolyzed under basic conditions,reduced with potassium borohydride to obtainδ-hydroxycarboxylic acid,and finally acid-catalyzed Intramolecular esterification ofδ-hydroxy carboxylic acid to form a racemic octahydrocoumarin derivative,5,7,7-trimethyl-octahydro-2H-benzopyran-2-one;The target compound were characterized by IR,1H NMR,13 C NMR and MS.
作者
侯峰
裴继红
黄战鏖
HOU Feng;PEI Jihong;HUANG Zhan’ao(Shanghai Wanxiang Flavors&Fragrances Co.,Ltd.,Shanghai 201318,China)
出处
《应用技术学报》
2020年第4期339-342,374,共5页
Journal of Technology
