Acta Scientiarum Naturalium Universitatis Pekinensis

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

LIN Chongxi,LIU Jingyuan,WANG An,YE Xiulin   

  1. College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871
  • Received:2001-10-31 Online:2002-11-20 Published:2002-11-20



  1. 北京大学化学与分子工程学院,北京,100871

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]D25-45.03 °,DMSO]), its amide derivative s 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 o f 1~6 were elucidated by the polarization ability of functional gro ups and the helical structures.

Key words: tartaric acid derivatives, helical structure, specific rotation, optical activity

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]D25+3.00°,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]D25-45.03 °,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:-0.52°, 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。

关键词: 酒石酸衍生物, 螺旋结构, 比旋光度, 光学活性

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