1,1’-联萘-2,2’-二酚及其孟基碳酸酯衍生物的手性高效液相色谱  

Chiral Resolution of 1,1'-binaphthalene-2,2'-diol and its (-)- Menthyl Chloroformate Derivatives by High Performance Liquid Chromatography with Urea Derivative as Chiral Stationary Phase

作　　者：阮源萍[1,2] 敖小平 陈安齐[2] 黄培强[2] 靳立人[2] 

机构地区：[1]厦门大学现代分析科学教育部重点实验室,福建厦门361005 [2]厦门大学化学系,福建厦门361005

出　　处：《厦门大学学报（自然科学版）》2002年第2期217-221,共5页Journal of Xiamen University：Natural Science

基　　金：国家自然科学基金资助项目 (2 9832 0 2 0 )

摘　　要：用高效液相色谱法考察了 1,1’ 联萘 2 ,2’ 二酚及其单和双氯代孟基碳酸衍生物等三对手性化合物在 (S) 特 亮氨酸基 (S) 1 (α 萘基 )乙胺脲型手性色谱柱上的拆分行为 .讨论了三元流动相中 1,2 二氯乙烷和乙醇含量的变化以及不同极性调节剂对分离的影响 ,探讨了这些手性化合物在脲型手性固定相上的可能拆分机理 .该法已用于 ( ) 孟基氯代碳酸酯化学拆分外消旋 1,1’ 联萘 2 ,2’The chiral resolution of 1,1'-binaphthalene-2,2'-diol (1), 1,1'-binaphthalene-2,2'-diol-mono-[(-)-menthyl] carbonate(2) and 1,1'-binaphthalene-2,2'-diol-bi-[(-)-menthyl] carbonate(3) was studied by high performance liquid chromatography using (S)-tert-leucine and (S)-1-α-NEA as chiral stationary phase. The effect of different content of 1,2-dichloroethane and ethane, as well as a different polar modifier in mobile phase on the chiral separation was discussed. A baseline separation of optical isomers of compounds 1 and 2 with n-hexane/1,2- dichloroethane/ethanol(82∶16∶2, V/V/V) as mobile phase was obtained. The optical isomers first eluted are S-2 and R-1, their capacity factors are 0.159 and 1.196, separation factors are 1.779 and 1.311,resolutions are 2.444 and 4.266, respectively. The optical isomers of compound 3 are only partially resolved. The likely role of double hydrogen bonding between 1,1'-binaphthalene-2,2'-diol and (S)-tert-leucine & (S)-1-α-NEA as well as steric hindrance for the chiral recognition and separation was discussed. This method was applied to identify the optical purity of the samples from the resolution of racemic 1,1'-binaphthalene-2,2'-diol.

关 键 词：手性高效液相色谱 手性拆分 脲型手性固定相 氯代孟基碳酸酯衍生物 1 1'-联萘-2 2’-二酚 光学纯度 

分 类 号：O625.313[理学—有机化学] O657.72[理学—化学]