含双催化中心手性配体的合成

论文编号:HG160  论文字数:14330,页数:33

摘 要：手性氨基醇在不对称合成和药物中间体领域的广泛应用，已经引起了众多科研人员的浓厚兴趣。本论文在查阅相关资料的基础上综述了不对称催化还原反应的研究新进展。
 为寻找性能优异的催体，基于多催化中心配体在不对称催化还原反应中的协同效应，可获得手性氨基醇较高的e.e.值。我们分别使用了天然麻黄碱（-）和（1R，2S）-（-）及（1S，2R）-（+）-2-氨基-1，2-二苯基乙醇为手性源与间二苄溴反应，经优化反应条件后在乙腈溶液中，于60-75℃下，以KI为催化剂，K2CO3为吸氢剂合成了二催化中心配体：N-甲基-N-(1′S,2′R)-(1′-甲基-2′苯基-2′-羟基)乙基-间二苄胺；N-(1′R,2′S)-(1′,2′二苯基-2′-羟基)和N-(1′S,2′R)-(1′,2′二苯基-2′-羟基)乙基-间二苄胺，经硅胶柱色谱纯化得无色晶体，产率较高。产物经IR、MS和1HNMR等确认，其他物理常数也较理想。

关键词：手性氨基醇；麻黄碱；配体；合成；提纯

Abstract: Chiral amino alcohol has extensively applicates  in the asymmetric synthesis and intermediate areas, and a lot of scientific research personnel  have deep interests in it . In this paper, the inspection on the basis of the relevent information summarizes the asymmetric catalytic reduction of new progress.
 In order to find high performance, based on more catalysis center ligand in asymmetric catalytic reduction of synergies, can achieve available chiral secondary alcoholshigher e.e. value. We were using the natural ephedrine (-), (1 R, 2S )-(-) and (1 S, 2R )-(+)- 2 - amino-1,2 - diphenyl ethanol as chiral sources with 1,3- benzyl bromide reaction by optimizing reaction conditions in ethanol solution, in the 60-75 ℃, KI as a catalyst, K2CO3 as a hydrogen absorption reagent first synthesized the catalysis center with the ligand: N-methyl-N-(1′S, 2′R)-(1′-methyl-phenyl-2′- hydroxy) ethyl -1′,3′ benzylamine; N-(1′R, 2′S)-(1′,2 ′diphenyl -2′- hydroxy) and N-(1′S, 2′R)-(1′,2 ′diphenyl -2 ′- hydroxy) ethyl–1′,3′ benzylamine, by silica gel column chromatography get the colorless crystal, yields are higher. Product by the IR、MS and 1HNMR,etc. confirmed.The other physical constants are good.

Keywords：chiral amino alcohol;  ephedrine;  ligand;  synthesis;  purification

目  录
中文摘要 I
英文摘要 II
目录 III
1. 绪论 1
 1.1  手性化合物的应用 2
 1.2 获得手性化合物的方法 3
 1.3 手性技术的影响 5
 1.4 手性氨基醇 5
2. 实验部分 8
 2.1 实验仪器 8
 2.2 实验试剂和原料 .8
 2.3合成路线设计 9
 2.4 目标产物 9
 2.5 实验过程 10
3. 结果与讨论 15
 3.1 实验结果 15
 3.2 实验讨论 20
4．总结与展望 22
致谢 23
参考文献 24
附录 26