含硫香料——硫代芳樟醇及其衍生物的合成研究

THIO-CONTAINING FLAVORING : STUDIES ON THE SYNTHESIS OF THIOLINALOOL AND ITS DERIVATIVES

本文对香叶醇转化为硫代芳樟醇(4)及其衍生物的合成方法进行了研究。香叶醇与N,N-二甲基琉代氨基甲酰氯反应生成N,N—二甲基琉代氨基甲酸-O-香叶基酯(5),(5)通过[3,3]-σ迁移反应转变成N,N-二甲基硫代氨基甲酸-S-芳樟基酯(6),(6)进一步还原得到硫代芳樟醇(4)。(4)转变成衍生物硫代芳樟醇乙酸酯(7a)及芳樟基甲基疏醚(7b)。(4)及(7b)在高度稀释时具有愉快的热带水果香味。

The paper describes a synthetic method of thiolinalool (4) and its derivatives. O-geranyl dimethylthiocarbamate(5)was prepared by the reaction of geraniol with dimethylthiocarbamoyl chloride. (5)was changed into S-linalyl dimethylthiocarbamatc(6)by [3,3]-σrearrangement. (6)can be reduced to(4)by using LiAlH4 and (4) gives its derivatives(7a)and (7b)under different conditions. At low concentration, (4)and (7b)possess aroma flavor of tropical fruits.