6,6'-二甲氧基-4,5,4',5'-二亚甲基二氧基-2,2'-联苯二甲酸二甲酯及其衍生物的合成研究

Syntheses Studies of 6,6'-Dimethoxy-4,5,4',5'-dimethenedioxy-2,2'-dimeth oxycarbonyl Biphenyl and Its

以没食子酸为原料经酯化、醚化、区域选择性硝化、还原、Sandmeyer及分子间 Ulmann耦合等反应以较高产率合成了 6,6 -二甲氧基 -4 ,5 ,4 ,5 -二亚甲基二氧基 -2 ,2 -联苯二甲酸二甲酯 (β-联苯双酯 ,β-DDB) ,并对其进行衍生化 ,得到 5个β-DDB的衍生物 ,用 IR,1 H NMR和 MS等鉴定了其结构 ,使用手性柱对β-DDB进行拆分得到了两个对映异构体 。

The present paper covered the syntheses of 6,6 dimethoxy 4,5,4,5 dimethenedioxy 2,2 dimethoxycabonyl biphenyl( β DDB) in higher yield with the gallic acid as the starting material by multi step synthesis: esterification, monomethylation, formation of the methylenedioxy derivative, nitration, reduction, Sandmeyer and Ullmann coupling reaction. Five of its derivatives have also been synthesized and four of them are new compounds. The structure of these compounds are confirmed by IR, 1H NMR, MS and EA. The resolution of β DDB with HPLC gave two components. The configuration of the first component was assigned as R by comparison of its CD spectrum. 258 positive cotton effect with that of R dimethyl hexamethoxydiphenate, and the configuration of the second component thus obtained was assigned as S by comparison of its CD spectrum 258 negative Cotton Effect.