基于2(5H)-呋喃酮的C-C成键反应研究进展

doi:10.6023/cjoc201803053

有机化学 ›› 2018, Vol. 38 ›› Issue (8): 1872-1884.DOI: 10.6023/cjoc201803053 上一篇下一篇

综述与进展

基于2(5H)-呋喃酮的C-C成键反应研究进展

王柏文^a, 刘园^a, 郝志峰^b, 侯佳琦^a, 李健怡^a, 李舒婷^a, 潘思慧^a, 曾铭豪^a, 汪朝阳^a

a 华南师范大学化学与环境学院教育部环境理论化学重点实验室广州 510006;
b 广东工业大学轻工化工学院广州 510006

收稿日期:2018-03-30 修回日期:2018-04-29 发布日期:2018-05-14
通讯作者: 郝志峰, 汪朝阳 E-mail:haozhifeng3377@163.com;wangzy@scnu.edu.cn
基金资助:
华南师范大学大创计划（No.20181442）、广东省自然科学基金（No.2014A030313429）、广州市科技计划科学研究专项（No.201607010251）、广东省应用型科技研发专项资金（No.2016B090930004）及广东省科技计划（No.2017A010103016）资助项目.

Recent Progress in C-C Bond Construction Based on 2(5H)-Furanone

Wang Bowen^a, Liu Yuan^a, Hao Zhifeng^b, Hou Jiaqi^a, Li Jianyi^a, Li Shuting^a, Pan Sihui^a, Zeng Minghao^a, Wang Zhaoyang^a

a School of Chemistry and Environment, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006;
b School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006

Received:2018-03-30 Revised:2018-04-29 Published:2018-05-14
Contact: 10.6023/cjoc201803053 E-mail:haozhifeng3377@163.com;wangzy@scnu.edu.cn
Supported by:
Project supported by the Undergraduates Innovation Project of South China Normal University (No. 20181442), the Natural Science Foundation of Guangdong Province (No. 2014A030313429), the Guangzhou Science and Technology Project Scientific Special (No. 201607010251), the Applied Science and Technology Research and Development Special Foundation of Guangdong Province (No. 2016B090930004) and the Guangdong Provincial Science and Technology Project (No. 2017A010103016).

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摘要/Abstract

2（5H）-呋喃酮具有多个反应位点，同时其骨架广泛存在于许多天然产物的结构中，因此2（5H）-呋喃酮的衍生化反应具有重要的研究意义.一些简单的2（5H）-呋喃酮分子，如3-位（或4-位）卤代的2（5H）-呋喃酮、5-位无取代基的2（5H）-呋喃酮以及4-羟基-2（5H）-呋喃酮及其衍生物等，可以与有机金属化合物、卤代烃、有机硼化合物、不饱和烃以及不饱和C=X（X=O、N）等多种试剂作用，分别在2（5H）-呋喃酮骨架的3-位、4-位、5-位等不同位置上构建C-C键.鉴于此，以反应试剂为分类依据，综述了近年来基于2（5H）-呋喃酮骨架的C-C成键反应，总结了它们在有机合成方法学中及其生物活性化合物合成应用中的新进展，并指出进一步实现2（5H）-呋喃酮C-C成键反应的绿色化及其高效多环化利用是未来的重要研究方向.

关键词: 2(5H)-呋喃酮, C-C键构建, 金属催化偶联反应, 有机小分子催化Vinylogous型反应, 多环化反应

2(5H)-Furanone contains several reaction points, and its structure unit exists in a number of nature products, which makes the researches on the derivatizations of 2(5H)-furanone important. Some 2(5H)-furanone compounds, such as 3-(or 4-) halo-2(5H)-furanone, 5-nonsubstitued 2(5H)-furanone, 4-hydroxy-2(5H)-furanone and their derivatives, can react with organometallic reagents, alkyl halides, organoboron compounds, unsaturated hydrocarbons and unsaturated C=X (X=O, N) compounds, forming C-C bond at 3-, or 4-, or 5-position of 2(5H)-furanone, respectively. According to the different types of reagents, the C-C bond formation reactions based on 2(5H)-furanone synthons are reviewed, and their recent progress in organic synthesis methodology and application of bioactive compounds is summarized. In the future, it is important to make the 2(5H)-furanone C-C bond formation reaction more greener and efficiently used in polycyclization reaction.

Key words: 2(5H)-furanone, C-C bond formation, metal-catalyzed coupling reaction, organocatalytic vinylogous reaction, polycyclization reaction

引用此文

王柏文, 刘园, 郝志峰, 侯佳琦, 李健怡, 李舒婷, 潘思慧, 曾铭豪, 汪朝阳. 基于2(5H)-呋喃酮的C-C成键反应研究进展[J]. 有机化学, 2018, 38(8): 1872-1884.

Wang Bowen, Liu Yuan, Hao Zhifeng, Hou Jiaqi, Li Jianyi, Li Shuting, Pan Sihui, Zeng Minghao, Wang Zhaoyang. Recent Progress in C-C Bond Construction Based on 2(5H)-Furanone[J]. Chin. J. Org. Chem., 2018, 38(8): 1872-1884.

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基于2(5H)-呋喃酮的C-C成键反应研究进展

Recent Progress in C-C Bond Construction Based on 2(5H)-Furanone

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