[1]吴和义,魏梅红,陶艳红,等.聚乙二醇负载苯硒基乙酸酯试剂参与5-取代-α,β-丁烯酸内酯的液相合成研究[J].江西师范大学学报(自然科学版),2016,40(05):537-541.
 WU Heyi,WEI Meihong,TAO Yanhong,et al.The Liquid-Phase Organic Synthesis of 5-Substituted-α,β-Butenolides Based on Poly(Ethylene Glycol)Supported Phenylselenoacetate Reagent[J].,2016,40(05):537-541.
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聚乙二醇负载苯硒基乙酸酯试剂参与5-取代-α,β-丁烯酸内酯的液相合成研究()
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《江西师范大学学报》(自然科学版)[ISSN:1006-6977/CN:61-1281/TN]

卷:
40
期数:
2016年05期
页码:
537-541
栏目:
出版日期:
2016-10-01

文章信息/Info

Title:
The Liquid-Phase Organic Synthesis of 5-Substituted-α,β-Butenolides Based on Poly(Ethylene Glycol)Supported Phenylselenoacetate Reagent
作者:
吴和义魏梅红陶艳红刘晓玲
江西师范大学化学化工学院,江西 南昌 330022
Author(s):
WU HeyiWEI MeihongTAO YanhongLIU Xiaoling
Institutes of Chemistry and Chemical Engineering,Jiangxi Normal University,Nanchang Jiangxi 330022,China
关键词:
聚乙二醇负载苯硒基乙酸酯 5-取代-αβ-丁烯酸内酯 液相有机合成
Keywords:
PEG supported phenylselenoacetate ester 5-substituted-αβ-butenolides liquid-phase organic synthesis
分类号:
O 625
摘要:
在4-二甲胺基吡啶和N,N’-二环己基碳二亚胺存在下,苯硒基乙酸与二羟基聚乙二醇(相对分子质量为4 000)发生酯化反应,制得聚乙二醇负载的苯硒基乙酸酯(功能基含量为 0.455 mmol Se·g-1)试剂.该试剂与N,N-二异丙胺基锂作用后,与环氧化合物发生开环反应,不经分离,直接加入质量分数为30%的双氧水进行氧化脱硒,形成中间体聚乙二醇负载γ-羟基-α,β-不饱和羧酸酯,继而用对甲苯磺酸催化环化反应,得到5-取代-α,β-丁烯酸内酯,产率优良(80%~86%).
Abstract:
Reaction of difunctional poly(ethylene glycol)(PEG)4 000 with phenylselenoacetic acid in anhydrous dichloromethane in the presence of 1,3-dicyclohexylcarbodiimide and 4-dimethylaminopyridine readily gave rise to PEG supported phenylselenoacetate ester,which was reacted with lithium diisopropylamide,followed successively by treatment with epoxide and 30% hydrogen peroxide afforded PEG supported γ-hydroxy-α,β-unsaturatecarboxylic acid ester intermesiates.Subsequent cleavage from the PEG using p-toluenesulfonic acid in refluxing toluene afford 5-substituted-α,β-butenolides with good yields(80%-86%).

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备注/Memo

备注/Memo:
收稿日期:2016-04-11基金项目:国家自然科学基金(20562002),江西省教育厅科研基金(GJJ11380)和国家单糖化学合成工程技术研究中心开放基金(GJDTZX-KF-201414)资助项目.通信作者:刘晓玲(1967-),女,江西永新人,教授,主要从事功能高分子的研究.
更新日期/Last Update: 1900-01-01