2-苯基-1-环丙烷羧酸酯对映体的毛细管气相色谱分离研究

Capillary Gas Chromatographic Separation of Enantiomers of 2-Phenyl-1-Cyclopropanecarboxylate

使用3 位酰基化的4种2,6 二 O 戊基 3 O 酰基化 β 环糊精衍生物和6 位酰基化的3种2,3 二 O 戊基 6 O 酰基化 β 环糊精衍生物作为毛细管气相色谱手性固定相,对4对2 苯基 1 环丙烷羧酸酯对映体(cis 2 PhCpOMe,cis 2 PhCpOEt,trans 2 PhCpOMe,trans 2 PhCpOEt)进行分离研究。结果表明,对所拆分的4对2 苯基 1 环丙烷羧酸酯对映体而言,3 位酰基化的4种2,6 二 O 戊基 3 O 酰基化 β 环糊精衍生物比6 位酰基化的3种2,3 二 O 戊基 6 O 酰基化 β 环糊精的对映体分离能力更强。顺式结构的2 苯基 1 环丙烷羧酸酯(cis 2 PhCpOMe,cis 2 PhCpOEt)对映体比相应反式结构的2 苯基 1 环丙烷羧酸酯(trans 2 PhCpOMe,trans 2 PhCpOEt)对映体与4种2,6 二 O 戊基 3 O 酰基化 β 环糊精固定相的作用更有利于对映体分离;2 苯基 1 环丙烷羧酸甲酯(cis 2 PhCpOMe,trans 2 PhCpOMe)比其乙酯(cis 2 PhCpOEt,trans 2 PhCpOEt)与环糊精衍生物固定相的作用更有利于手性分离。

Four pairs of enantiomers of methyl cis and trans2phenyl1cyclopropanecarboxylates, and ethyl cis and trans2phenyl1cyclopropanecarboxylates were resolved on capillary gas chromatographic columns using four 2,6diOpentyl3Oacylatedβcyclodextrins and three 2,3diOpentyl6Oacylatedβcyclodextrins as chiral stationary phases. The separation results show that the four 2,6diOpentyl3Oacylatedβcyclodextrins possess stronger enantioselectivity than the three 2,3diOpentyl6Oacylatedβcyclodextrins for the four pairs of enantiomers studied. It is also found that methyl cis and trans2phenyl1cyclopropanecarboxylates were separated better than ethyl cis and trans2phenyl1cyclopropanecarboxylates on the four 2,6diOpentyl3Oacylatedβcyclodextrin columns; methyl and ethyl cis2phenyl1cyclopropanecarboxylates were better separated than its corresponding methyl and ethyl trans2phenyl1cyclopropanecarboxylates. 