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新型4-羟基香豆素烯醚衍生物的合成
引用本文:苏秋玲,钱后俊,王治明.新型4-羟基香豆素烯醚衍生物的合成[J].合成化学,2017,25(6):493-497.
作者姓名:苏秋玲  钱后俊  王治明
作者单位:常州大学 石油化工学院,江苏 常州 213164
基金项目:国家自然科学基金资助项目,江苏省高校自然科学研究重大资助项目,江苏省青蓝工程项目
摘    要: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rn(2-丁炔酸乙酯,2a) : n(4-羟基香豆素,1a)]、溶剂、催化剂、反应温度和反应时间对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%)。

关 键 词:4-羟基香豆素  Michael加成  烯醚衍生物  路易斯碱催化  合成  
收稿时间:2016-11-25

Synthesis of Novel 4-Hydroxycoumarin Vinyl Ether Derivatives
SU Qiu-ling,QIAN Hou-jun,WANG Zhi-ming.Synthesis of Novel 4-Hydroxycoumarin Vinyl Ether Derivatives[J].Chinese Journal of Synthetic Chemistry,2017,25(6):493-497.
Authors:SU Qiu-ling  QIAN Hou-jun  WANG Zhi-ming
Institution:School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
Abstract: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 rn(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].
Keywords:4-hydroxycoumarin  Michael addition  vinyl ether derivative  Lewis base catalyst  synthesis
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