摘要
本文以(S)-二乙基(1-重氮-2-(1,3-二氧化异吲哚酮-2-基)丙基)膦酸酯(化合物a)为原料,以5%Pd/C为催化剂,在冰乙酸、异丙醇存在下加氢还原,成功制得了(S)-二乙基(2-(1,3-二氧化异吲哚酮-2-基)丙基)膦酸酯(化合物b),即手性β-氨基膦酸酯,并探讨了催化剂5%Pd/C加入量,冰乙酸用量以及反应时间对试验的影响,得出了制备化合物b的较佳条件.即:化合物a∶催化剂5%Pd/C∶冰乙酸的物质的量比为1∶0.2∶0.6,反应时间为2 h;同时化合物b通过1HNMR、13CNMR、31PNMR、MS的测定,进行结构表征,结构正确;最后计算出化合物b的ee值为94.5%.
This paper using(S)-diethyl(1-diazo-2-(1,3-dioxoisoindolin-2-yl)propyl)phosphonate as starting material which catalysted by 5%Pd-C, prepared(S)-diethyl(2-(1,3-dioxoisoindolin-2-yl)propyl)phosphonate in the presence of glacial acetic acid and i-Pr OH. The effect of catalyst amount, the glacial acetic acid amount and the reaction time were discussed. The results indicate that the optimum conditions were the ratio of compound a, 5%Pd-C and glacial acetic acid was 1∶0.2∶0.6 and reacted 2 h. The obtained compound b was identified by1 HNMR,13CNMR,31 PNMR and MS and the enantiomeric excess was94.5%.
出处
《天津理工大学学报》
2015年第2期10-13,共4页
Journal of Tianjin University of Technology
基金
国家自然科学基金(21072102)
关键词
氢化还原
手性
β-氨基膦酸酯
hydrogenation reduction
chiral
β-amino phosphonate