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酒石酸衍生物的合成及其结构与光学活性关系的探讨

Studies on the Relationship between the Structures of TartaricAcid Derivatives and Their Optical Activities

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【作者】 林崇熙柳敬元王安叶秀林

【Author】 LIN Chongxi LIU Jingyuan WANG An YE Xiulin (College of Chemistry and Molecular Engineering, Peking University,Beijing,100871)

【机构】 北京大学化学与分子工程学院北京大学化学与分子工程学院 北京100871北京100871

【摘要】 合成出系列的L 半螺旋型酒石酸衍生物 1~ 6 ,测定比旋光度 ,发现酒石酸二乙酯 2 ([α]2 5D+ 3 0 0° ,DMSO)形成 2 ,3 O 亚异丙基酒石酸二乙酯 3后旋光急剧往左偏移 ([α]2 5D - 4 5 0 3° ,DMSO) ,3酰胺化后比旋光值往右偏移 (4a :+ 11 19° ,4b :+ 2 14°) ,还原产物的比旋光值往左偏移 (5a :- 0 5 2° ,5b :- 4 92° ,6 :- 2 95°) ;并用分子的螺旋结构与基团的极化性质研究旋光规律

【Abstract】 Several L-tartaric acid derivatives (1~6) were synthesized and their specific rotations were measured.It was found that diester 3 exhibited an unusually high negative value of specific rotation ([α] 25 D-45 03°,DMSO),its amide derivatives 4 showed slightly positive specific rotation (4a:+11^19°,4b:+2 14°),and the reduction products showed slightly negative values (5a:-0 52°,5b:-4 92°,6:-2 95°).The optical activities of 1~6 were elucidated by the polarization ability of functional groups and the helical structures.

  • 【文献出处】 北京大学学报(自然科学版) ,Acta Scicentiarum Naturalum Universitis Pekinesis , 编辑部邮箱 ,2002年06期
  • 【分类号】O623
  • 【被引频次】6
  • 【下载频次】418
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