高效液相色谱手性固定相法拆分BETTI碱及其衍生物对映体

在纤维素三（3,5-二甲基苯基氨基甲酸酯）（Chiralcel OD-H）和Pirkle型(R, R)-Whelk-O1手性柱上对手性氨基酚1-(α-氨基苄基)-2-萘酚（Betti 碱）及其衍生物1-(α-苄氨基苄基)-2-萘酚和1-(α-哌啶基苄基)-2-萘酚对映体分离进行了研究，分别考察了在正己烷流动相中，碱性添加剂、醇类添加剂的种类和浓度对手性拆分的影响。结果表明：溶质在Chiralcel OD-H柱上的分离效果好，而在(R, R)-Whelk-O1手性柱上只有1-(α-苄氨基苄基)-2-萘酚部分分离。研究了空间立体结构因素对手性分离的影响，初步探讨和比较了溶质在这2种手性柱上的手性识别机理。发现对(R, R)-Whelk-O1柱，溶质与固定相之间的吸引作用很小，而对于Chiralcel OD-H柱，溶质在手性空腔中的空间适应性很可能是手性识别的关键。

Enantioseparation of Betti bases on chiral stationary phase by HPLC

In this paper, the separation of 1-(α-aminobenzyl)-2-naphthol, 1-(α-benzylaminobenzyl)-2-naphthol and 1-(α-piperidylbenzyl)-2-naphthol is studied on two chiral columns-Chiralcel OD-H and (R,R)-Whelk-O1 chiral columns. The influence of the structures on the chiral separation is investigated. The influence of the mobile phase composition including the concentration and type of the alcohol modifiers and the basic additive in hexane, the separation factor (α) and the resolution (Rs) are studied. Then the two different chiral recognition mechanisms are discussed and compared. 1-(α-aminobenzyl)-2-naphthol and 1-(α-benzylaminobenzyl)-2-naphthol and 1-(α-piperidylbenzyl)-2-naphthol can be baseline separated on chiralcel OD-H using hexane-iso-propanol (95:5, v/v) as eluent under a flow rate of 0.5 mL·min^－1 at 25 °C. On (R,R)-Whelk-O1, the attractive interactions between CSP and solute are the key factor for retention and chiral recognition, on chiralcel OD-H, the steric fit of solute into the chiral cavity maybe the predominant factor for the chiral recognition of 1-(α-benzylaminobenzyl)-2-naphthol and 1-(α-piperidylbenzyl)-2-naphthol.