新型4-羟基香豆素烯醚衍生物的合成

摘要

Eleven novel 4-hydroxycoumarin vinyl ether derivatives(3a ～ 3k) were synthesized by Michael addition of 4-hydroxycoumarins compounds and ethyl 2-butynoate compounds under nitrogen atmosphere using DBU as the catalyst and acetonitrile as solvent.The structures were characterized by 1H NMR,13C NMR,IR and HR-MS(ESI).3a were confirmed to be a Z configuration by H-H NOESY.Effects of molar ratio r[n(2a):n(1a)],solvents,catalysts,temperature and reaction time were investigated.The results showed that the highest yield of 3a was 70％ under the optimum conditions [r=l.2,DBU as catalyst,reaction in CH3CN at 80 ℃ for 18 h].%氮气保护下,以4-羟基香豆素类化合物和2-丁炔酸酯类化合物为原料,1,8-二氮杂二环十一碳-7-烯(DBU)为催化剂,乙腈为溶剂,经Michael加成反应合成了11个新型4-羟基香豆素烯醚衍生物(3a～3k),其结构经1H NMR,13C NMR,IR和HR-MS (ESI)表征,其构型经H-H NOESY谱确定为Z构型.考察了投料比r[n(2-丁炔酸乙酯,2a)∶n(4-羟基香豆素,1a)]、溶剂、催化剂、反应温度和反应时闻对3a收率的影响.结果表明:在最优条件[r=1.2,乙腈为溶剂,DBU作催化剂,于80℃回流反应18 h]下,3a收率最高(70％).