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2024 , Vol. 44 >Issue 9: 2722 - 2731

DOI: https://doi.org/10.6023/cjoc20203013

综述与进展

氰基乙烯类化合物的制备与应用研究进展

  • 曾玉 ,
  • 黎忠昊 ,
  • 邓思威 ,
  • 陈祖佳 ,
  • 陈璧瑜 ,
  • 宇世伟 ,
  • 沈晴 ,
  • 汪朝阳
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  • 华南师范大学化学学院 教育部环境理论化学重点实验室 广州市生物医学分析化学重点实验室 GDMPA手性药物过程控制与质量评价重点实验室 广州 510006

收稿日期: 2024-03-12

  修回日期: 2024-04-15

  网络出版日期: 2024-05-10

基金资助

广东省基础与应用基础研究基金(2021A1515012342); 华南师范大学课外科研(23HXKB06); 华南师范大学课外科研(23HXKB01)

收起

Research Progress on Preparation and Application of Cyanoethylenes

  • Yu Zeng ,
  • Zhonghao Li ,
  • Siwei Deng ,
  • Zujia Chen ,
  • Biyu Chen ,
  • Shiwei Yu ,
  • Qing Shen ,
  • Zhaoyang Wang
Expand
  • Key Laboratory of Theoretical Chemistry of Environment of Ministry of Education, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, School of Chemistry, South China Normal University, Guangzhou, 510006, China
*E-mail: ;

Received date: 2024-03-12

  Revised date: 2024-04-15

  Online published: 2024-05-10

Supported by

Guangdong Basic and Applied Basic Research Foundation(2021A1515012342); Extracurricular Scientific Research Project of South China Normal University(23HXKB06); Extracurricular Scientific Research Project of South China Normal University(23HXKB01)

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摘要

氰基乙烯类是一类较易制备的π-π共轭化合物, 可通过Knoevenagel缩合反应、多组分反应、串联反应等绿色化方法获得. 氰基乙烯类中的特殊D-π-A类结构单元, 使其光学性质可应用于荧光探针、染料敏化电池中的敏化剂等领域. 同时, 氰基乙烯类化合物中β-位碳、氰基碳、γ-位碳电子云密度的不同影响着它们的化学反应性质, 使其可作为不同的合成子, 通过Michael加成型和环加成型等反应, 较温和地构建各种含氮化合物, 特别是环状化合物. 以合成氰基乙烯类化合物的类型为依据, 总结了其常见的制备策略; 按照在不同光学领域的应用, 介绍了氰基乙烯型荧光探针和电池敏化剂; 按照反应类型和产物结构, 综述了近年来其在有机合成领域的应用. 展望未来, 人们将会对其性能与应用有更多的了解, 设计更多性能优异的荧光探针分子, 同时深入发展氰基乙烯类化合物的有机合成应用.

关键词： 氰基乙烯; 荧光探针; 合成子; Michael加成型反应; 环加成型反应

本文引用格式

曾玉 , 黎忠昊 , 邓思威 , 陈祖佳 , 陈璧瑜 , 宇世伟 , 沈晴 , 汪朝阳 . 氰基乙烯类化合物的制备与应用研究进展[J]. 有机化学, 2024 , 44(9) : 2722 -2731 . DOI: 10.6023/cjoc20203013

Abstract

Cyanoethylenes are a class of easily prepared π-π conjugated compounds, which can be obtained by Knoevenagel condensation, multi-component reaction, tandem reaction and other green methods. The special D-π-A structural unit in cyanoethylene compounds makes their optical properties applicable to the fields such as fluorescent probes, sensitizers in dye-sensitized batteries, etc. At the same time, the difference in the electron cloud density of β-carbon, cyanocarbon, and γ-carbon in cyanoethylenes affects their chemical reaction properties, so that they can be used as different synthons to mildly construct various nitrogen-containing compounds, especially cyclic compounds through Michael type addition and cycloaddition type reactions. Based on the types of cyanoethylene compounds, their common preparation strategies are summarized. According to the applications in different optical fields, cyanoethylene-type fluorescent probes and battery sensitizers are introduced. The applications of cyanoethylenes in the area of organic synthesis in recent years are also reviewed in accordance with the reaction type and product structure. In the future, with the more understanding of the performance and application of cyanoethylenes, the more fluorescent probe molecules with excellent performance will be designed, and the further organic synthesis application of cyanoethylene compounds will be developed.

Key words： cyanoethylene; fluorescent probe; synthon; Michael type addition; cycloaddition type reaction

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