高效液相色谱法对反式-1,2-二取代环丙烷类化合物的手性拆分

Enantiomeric Resolution of trans 1,2 Disubstituted Cyclopropane by High Performance Liquid Chromatography

在ＣｈｉｒａｌｃｅｌＯＤ和ＣｈｉｒａｌｃｅｌＯＪ柱上，以各种配比的正己烷／异丙醇为洗脱剂，对１３种反式－１，２－二取代环丙烷类化合物的对映体进行了手性拆分。考察了这些外消旋物在这两种柱上的色谱行为。实验表明带芳环的反式－１，２－二取代环丙烷类化合物在ＯＤ及ＯＪ柱上的拆分能力明显地与芳环上取代基的性质和位置有关。另一方面，一些带有脂族取代基的反式－１，２－二取代环丙烷类化合物也能在这两种柱上得到拆分。实验显示，在手性拆分过程中，手性固定相与反式－１，２－二取代环丙烷类化合物之间的π－π或偶极－偶极作用等起着重要作用。

The enantiomeric resolution of racemic mixtures of thirteen trans 1,2 disubstituted cyclopropane was achieved with HPLC by using Chiralcel OD and Chiralcel OJ as chiral stationary phase and hexane/2 propanol mixtures with different concentrations as eluent. The chromatographic parameters of these racemates on Chiralcel OD and Chiralcel OJ columns were examined. The results showed that enantiomeric resolution ability of the racemic mixtures of trans 1,2 disubstituted cyclopropane on Chiralcel OD and Chiralcel OJ was strongly dependent on the site and the property of substituents on the benzene cycle. On the other hand, some racemates of trans 1,2 disubstituted cyclopropane with aliphatic group were also separated on the columns. The results showed that the chiral recognition process was the sum of all the possible chiral interaction (the dipole dipole,hydrogen bond hydrogen bond and π π interactions) between the chiral stationary phase and trans 1,2 disubstituted cyclopropane. This method has been applied to identify the optical purity of trans 1,2 disubstituted cyclopropane.