采用Chirex(S)-LEU&(S)-NEA、Chiralcel OD—H和Chiralpak AD—H手性色谱柱直接拆分了20羟基-1,1’-联萘-2-苯甲酸酯(HBNB)、1,1’-联萘-2,2’-二苯甲酸酯(BNDB)和2’-甲氧基-1,1’-联萘-2-苯甲酸酯(MBNB)对映体。分别考察了流动相组成、柱温和化合物结构对手性分离的影响。结果表明:3对联萘二酚苯甲酸酯对映体在Chiralpak AD—H柱上的拆分效果最好。当采用正己烷/异阿醇(40/60,v/v)为流动相时,HBNB、BNDB和MBNB对映体的分离因子(α)和分离度(Rs)分别为1.76、1.74、1.40和6.47、7.81、4.75.对比联萘二酚(BN)的分离,从联萘分子中2-位取代基、对映体出峰顺序和热力学参数等方面探讨了相关手性分离机理。
The enantioseparations of 2'-hydroxy-1, 1'-binaphthyl-2-yl benzoate ( HBNB), 1, 1 '- binaphthyl-2,2'-diyl dibenzoate (BNDB) and 2'-methoxy-1,1 '-binaphthyl-2-yl benzoate ( MB- NB) were studied on Chirex (S)-LEU & (S)-NEA, cellulose tris (3,5-dimethylphenylcarbamate) ( Chiralcel OD-H ) and amylose tris ( 3,5-dimethylphenylcarbamate ) ( Chiralpak AD-H ) columns, respectively, using high performance liquid chromatography. The effects of mobile phase, column temperature and compound structures on the enantioseparations were discussed. The Chiralpak AD-H exhibited stronger capability of enantioseparation in comparison with those of Chirex ( S)-LEU & ( S)-NEA and Chiralcel OD-H for 1, 1 '-bi-2-naphthol benzoates. When using the mobile phase of n-hexane/2-propanol (40/60, v/v), the chiral selectivi- ties of HBNB, BNDB and MBNB were 1.76, 1.74, and I. 40, respectively. Moreover, in comparison with that of 1,1 '-bi-2-naphthol ( BN), the mechanisms of the enantioseparation of 1,1 '- bi-2-naphthol benzoates, related to the substituted groups at 2-position, the elution orders and thermodynamic parameters were also discussed.