高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

2-亚烷基-5-羟甲基四氢呋喃的电化学合成

张程亮1, 雷泽1,2, 刘复初1, 祝正辉1, 蒋明忠1, 朱洪友1,2   

    1. 云南大学化学科学与工程学院, 教育部自然资源药物化学重点实验室, 昆明 650091;
    2. 昆明云大医药开发有限公司, 昆明 650222
  • 收稿日期:2008-05-13 修回日期:1900-01-01 出版日期:2009-03-10 发布日期:2009-03-10

Electrochemical Synthesis of 2-Alkylidene-5-hydroxymethyltetrahedrofunans

ZHANG Cheng-Liang1, LEI Ze1,2, LIU Fu-Chu1, ZHU Zheng-Hui1, JIANG Ming-Zhong1, ZHU Hong-You1,2*   

    1. Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, College of Chemical Science and Engineering, Yunnan University, Kunming 650091, China;
    2. Kunming Yunnan University Medical Development Co., Ltd., Kunming 650222, China
  • Received:2008-05-13 Revised:1900-01-01 Online:2009-03-10 Published:2009-03-10

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摘要： 以γ-烯基-β-酮酸酯为原料, KI-NaI为间接电解质, 水为溶剂及试剂, 利用电解合成的工艺方法, 以满意的收率和较高的选择性合成了13个2-亚烷基-5-羟甲基四氢呋喃化合物, 优化了合成条件, 并探讨了适宜的底物结构特征.

关键词: 2-亚烷基-5-羟甲基四氢呋喃, β-酮酸酯, 电化学合成, 绿色合成

Abstract: The structural unit of 2-alkylidene-5-hydroxymethyltetrahydrofunan exists in some natural compounds such as the macrotetrolide antibiotics and the ocean natural products Sarcodictyin and Eleutherobin. These natural compounds usually show outstanding biological activities. In this work we decribed a totally new method for the constructing of this structural unit by employing indirect electrolysis, namely, using KI and NaI as the indirect electrolyte, water as solvent and reagent, the γ-alkylation products of β-Ketoesters as the starting material. Thirteen kinds of 2-alkylidene-5-hydroxymethyltetrahydrofunans were synthesized in high yields and good selectivity. The success of this method has not only provided a “clean technology” of indirect electrolysis but also prompted a simple, effective and environmental friendly green synthesis.

Key words: 2-Alkylidene-5-hydroxymethyltetrahydrofunans, β-Ketoester, Electrochemical synthesis, Green synthesis

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