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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

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【作者】 郭瑞云何娟常俊标陈荣峰谢晶曦葛永辉刘月启

【Author】 GUO Rui Yun 1, HE Juan 1, CHANG Jun Bao 1  , CHEN Rong Feng 1 XIE Jing Xi 1, GE Yong Hui 1, LIU Yue Qi 2 (1. Henan Institute of Chemistry, Zhenzhou 450052; 2. Lanzhou Institue of Chemical Physics, Academia Sinica, Lanzhou 730000, C

【机构】 河南省化学研究所中国科学院兰州化学物理研究所 郑州450002郑州450002兰州730000

【摘要】 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 ,利用圆二色谱确定了它们的立体构型

【Abstract】 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.

【基金】 河南省杰出青年基金;国家新药研究基金 (批准号 :96 -90 1-0 5 -12 7)资助
  • 【文献出处】 高等学校化学学报 ,Chemical Research In Chinese Universities , 编辑部邮箱 ,2001年12期
  • 【分类号】O625
  • 【被引频次】10
  • 【下载频次】240
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