(R)-1-(3-(二苄基甲基氨基)-2-羟丙基)-1-甲基哌啶碘化铵的合成与应用  

Synthesis and application of(R)-1-(3-(dibenzylmethylamino)-2-hydroxypropyl)-1-methylpiperidine ammonium iodide

作　　者：张劲 胡拥军 彭天英 刘赛文 ZHANG Jin;HU Yongjun;PENG Tianying;LIU Saiwen(School of Materials and Chemical Engineering,Hunan City University,Yiyang,Hunan 413000,China)

机构地区：[1]湖南城市学院材料与化学工程学院,湖南益阳413000

出　　处：《湖南城市学院学报（自然科学版）》2023年第2期68-72,共5页Journal of Hunan City University:Natural Science

基　　金：湖南省教育厅科研项目(22A0553)。

摘　　要：首先,以二苄胺和(R)-环氧氯丙烷为原料合成了(R)-3-二苄胺基-1,2-环氧丙烷,再与哌啶反应合成了(R)-1-二苄胺基-3-哌啶基-2-丙醇(ligand 1),并研究了ligand 1诱导二乙基锌对苯甲醛的对映选择性加成反应;其次,用(R)-1-二苄胺基-3-哌啶基-2-丙醇和碘甲烷反应合成了(R)-1-(3-(二苄基甲基氨基)-2-羟丙基)-1-甲基哌啶碘化铵(ligand 2),同时研究了ligand 2在不对称相转移催化反应中的应用,并利用核磁共振对上述产物进行了表征.试验结果显示,上述手性配体均具有一定的不对称诱导效果.(R)-1-(dibenzylamino)-3-(piperidin-1-yl)propan-2-ol(ligand 1)was obtained by the reaction of piperidine with(R)-3-dibenzylamine-1,2-epoxy propane which was synthesized from dibenzyl amine and(R)-epichlorohydrin.Then,the ligand 1 was used to induce asymmetric addition of diethyl zinc to benzaldehyde.And then,the corresponding chiral quaternary ammonium salt(ligand 2)based on(R)-1-(dibenzylamino)-3-(piperidin-1-yl)propan-2-ol was obtained,used as ligand in phase transfer catalytic asymmetric reaction was carried out.The compounds mentioned above were characterized by NMR.The experimental results show that the above chiral ligands have a certain asymmetric induction effect.

关 键 词：合成 手性胺醇 手性季铵盐 不对称催化 

分 类 号：O62[理学—有机化学]