改进的(S)-3,3'-二(吡咯烷甲基)-八氢联萘酚合成方法  

Improved Synthetic Method of(S)-3,3'-Di(pyrrolidinylmethyl)-H_(8)BINOL

作　　者：符世玮 葛锐 汤佳凡 明巍 古双喜[1] FU Shiwei;GE Rui;TANG Jiafan;MING Wei;GU Shuangxi(School of Chemical Engineering and Pharmacy,Wuhan Institute of Technology,Wuhan 430205,China)

机构地区：[1]武汉工程大学化工与制药学院,湖北武汉430205

出　　处：《武汉工程大学学报》2021年第2期124-127,共4页Journal of Wuhan Institute of Technology

基　　金：国家自然科学基金(21877087);武汉工程大学研究生创新基金(CX2019008)。

摘　　要：(S)-3,3'-二(吡咯烷甲基)-八氢联萘酚可广泛应用于不对称催化反应和手性分子识别,但其合成方法仍有待改进。以(S)-联萘酚为原料,通过环境友好的两步反应在乙醇溶剂中合成了(S)-3,3'-二(吡咯烷甲基)-八氢联萘酚。在(S)-联萘酚的氢化反应中,研究了钯的负载量及其回收套用,发现在质量分数1%~5%(钯净含量占原料)的钯炭催化剂的作用下,反应收率均几乎定量,但所需反应时间不同。在类曼尼希反应中,开发了改进的合成方法,不仅溶剂更为绿色,而且后处理方法更为简单、高效和省时,产品收率高达97.9%。(S)-3,3'-di(pyrrolidinylmethyl)-octahydrobinaphthol can be widely used in asymmetric catalytic reactions and chiral molecular recognition,but its synthesis method still needs improvement.(S)-3,3'-di(pyrrolidinylmethyl)-octahydrobinaphthol was synthesized through an environment-friendly two-step reaction in ethanol solvent from(S)-binaphthol.In the hydrogenation reaction of(S)-binaphthol,the loading amount of Pd,the recycling and reusing of catalyst were studied.It was found that the yield is almost quantitative under 1%-5%Pd[the net weight of Pd relative to(S)-binaphthol in different reaction time].In the Mannich-type reaction,an improved synthesis method was developed.The solvent is greener,the post-treatment method is simpler,more efficient and time-saving,moreover,the product yield is as high as 97.9%.

关 键 词：(S)-3 3'-二(吡咯烷甲基)-八氢联萘酚 手性催化剂 类曼尼希反应 绿色溶剂 

分 类 号：O622.6[理学—有机化学]