高等学校化学学报

高等学校化学学报 ›› 2001, Vol. 22 ›› Issue (12): 2018.

• 研究论文 • 上一篇    下一篇

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

郭瑞云1, 何娟1, 常俊标1, 陈荣峰1, 谢晶曦1, 葛永辉1, 刘月启2   

  1. 1. 河南省化学研究所, 郑州 450002;
    2. 中国科学院兰州化学物理研究所, 兰州 730000
  • 收稿日期:2000-08-19 出版日期:2001-12-24 发布日期:2001-12-24
  • 通讯作者: 常俊标(1963年出生),男,博士,研究员,博士生导师,主要从事药物合成研究.E-mail:jbchang@public2.zz.ha.cn E-mail:jbchang@public2.zz.ha.cn
  • 基金资助:

    河南省杰出青年基金;国家新药研究基金(批准号:96-901-05-127)资助

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

GUO RuiYun1, HE Juan1, CHANG JunBao1, CHEN RongFeng1, XIE JingXi1, GE YongHui1, LIU YueQi2   

  1. 1. Henan Institute of Chemistry, Zhenzhou 450052;
    2. Lanzhou Institue of Chemical Physics, Academia Sinica, Lanzhou 730000, China
  • Received:2000-08-19 Online:2001-12-24 Published:2001-12-24

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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,1HNMR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.

关键词: 硝化, 联苯, &beta, -联苯双酯, Ullmann耦合反应

Abstract: The present paper covered the syntheses of 6,6' dimethoxy 4,5,4',5' dimethenedioxy 2,2' dimethoxycabonyl biphenyl( βDDB) 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, 1HNMR, MSand EA. The resolution of βDDBwith HPLCgave two components. The configuration of the first component was assigned as Rby comparison of its CDspectrum. 258 positive cotton effect with that of Rdimethyl hexamethoxydiphenate, and the configuration of the second component thus obtained was assigned as Sby comparison of its CDspectrum 258 negative Cotton Effect.

Key words: Nitration, Biphenyl, Biphenyl dicarboxylate, Ullmann coupling reaction

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