二氢(4,5)熏衣草醇的合成

Synthesis of Dihydro-4,5-lavandulol

叙述了以易得的异戊醇为原料合成熏衣草醇的一种新型二氢衍生物的方法。而异戊醇则可以从南中国的糖密发酵制造乙醇的蒸馏残液中得到。异戊基氯和丙酮的相转移催化缩合以43％的产率得到6-甲基-2-庚-酮,再经甲基化和脱氯化氢导致2,6-二甲基庚烯-2。该烯烃在氯化锡-二氯甲烷中,与多聚甲醛的Prins反应以41.2％的产率得到二氢(4,5)熏衣草醇。它似乎是有较淡熏衣草醇香气的类似物。

A synthetic route of the title compound, a new dihydrogenated derivative of lavendulol, starting with readily available isoanyl alcohol from the distillation residue in the ethanol production process with sugarhouse molasses in South China is described. Phase-tramsfer catalytic condensation of isoamyl chloride with acetone gave 6-methyl-2-heptanone in a yield of 43%, which upon methylation and dehydrochlorination led to 2, 6-dimethyl-2-heptene. Prins reaction of the alkene with paraformaldehyde in stannic chloride-dichloromethane afforded the final product in a yield of 41.2%. Dihydro (4,5) lavandulol seems to be a mimic with nice but a little milder lavender scent.