手性联萘酚功能化柱[5]芳烃的合成及手性识别  

Chiral BINOL Functionalized Pillar[5]Arenes:Synthesis and Chiral Molecular Recognition

作　　者：王繁盛 李璟雯 余冬艳 韦雪琴 黄雪秋 WANG Fan-sheng;LI Jing-wen;YU Dong-yan;WEI Xue-qin;HUANG Xue-qiu(School of Pharmacy,Guangxi Medical University,Nanning 530021,China)

机构地区：[1]广西医科大学药学院,广西南宁530021

出　　处：《化学试剂》2024年第11期114-120,共7页Chemical Reagents

基　　金：广西科技基地和人才专项项目(桂科AD21159001);广西自然科学基金项目(2021GXNSFBA196053);2023年广西硕士研究生创新项目(YCSW2023235)。

摘　　要：设计合成了手性联萘酚(BINOL)功能化的柱[5]芳烃3-R/S和6-R/S,通过核磁和质谱表征化合物结构。经HPLC拆分6-R获得非对映异构体6-RR p和6-RS p,进一步通过紫外滴定法测定6-RR p和6-RS p对R/S-1-苯乙醇和R/S-1-苯乙胺的结合常数,以探究手性联萘酚功能化的柱[5]芳烃对手性分子的选择性识别能力。结果表明,在柱[5]芳烃的一个苯环单元两侧修饰上大位阻基团能够阻止其翻转,通过手性HPLC拆分可获得具有手性的柱[5]芳烃非对映异构体。其中非对映体6-RR p对S-1-苯乙醇和R-1-苯乙醇的结合常数分别为1.2×10^(4)、2.6×10^(3) M-1,K s/K R=4.6,可选择性识别S-1-苯乙醇和R-1-苯乙醇。The BINOL functionalized pillar[5]arenes(P[5])3-R/S and 6-R/S were designed and synthesized,and further characterized by using NMR and MS.Compound 6 R was separated by chiral HPLC to obtain diastereomers of 6-RR P and 6-RS p.The binding constants of 6-RR P and 6-RS p to R/S-1-phenylethanol and R/S-1-phenethylamine were determined by UV titration to investigate the chiral molecular recognition ability of the chiral BINOL functionalized P[5].A pair of configurational diastereomers are generated by modifying the P[5]scaffold with bulky subunits and further chiral HPLC separation.The binding constants of 6-RR P with(S)-and(R)-1-phenylethanol are 1.2×10^(4) and 2.6×10^(3) M-1,respectively.The enantiomer 6-RR P can selectively recognize(S)-and(R)-1-phenylethanol with a K S/K R=4.6.

关 键 词：柱芳烃 手性联萘酚 超分子化学 手性识别 R/S-1-苯乙醇 

分 类 号：O65[理学—分析化学]