β-阿朴-12’-胡萝卜醛的合成研究

Synthesis of β-apo-12’-carotenal

阿朴-12’-胡萝卜醛,简称C25醛,可用于合成β-阿朴-8’-胡萝卜素酸乙酯、β-阿朴-8’-胡萝卜素醛、隐黄质和β-胡萝卜素,是合成类胡萝卜素的关键中间体。本文以十五碳膦酸酯为起始原料,先在二甲基亚砜钠盐的作用下转位为十五碳负离子,再与C10二醛发生HWE缩合反应,以高收率得到全反式含量高达95%以上且无三苯基氧膦残留的β-阿朴-12’-胡萝卜素醛固体,并考察各种反应因素对全反式含量和收率的影响。

Apo-12’-carotenal, referred to as C25 aldehyde, can be used to synthesize β-apo-8’-carotene ethyl ester, β-apo-8’-carotene aldehyde, cryptoxanthin and β-carotene. It is a key intermediate in the synthesis of carotenoids. In this paper, the pentadecyl phosphonate is used as the starting material, which is firstly translocated into pentadecane anion under the action of dimethyl sulfoxide sodium salt, and then undergoes HWE condensation reaction with C10 dialdehyde to obtain the complete product in high yield. The β-apo-12’-carotinal solid with trans content of more than 95 % and no triphenylphosphine oxide residues was obtained,and the effects of various reaction factors on the all-trans content and yield were investigated.