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2020 , Vol. 40 >Issue 5: 1105 - 1116

DOI: https://doi.org/10.6023/cjoc201912024

综述与进展

3,4-二取代-3-(二氟甲基)吡唑类化合物的构建

  • 曾俊良 ,
  • 许志红 ,
  • 马军安
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  • a 许昌学院化学化工学院 许昌 461000;
    b 天津大学化学系 天津市分子光电科学重点实验室 天津化学化工协同创新中心 天津 300072

收稿日期: 2019-12-18

  修回日期: 2020-02-03

  网络出版日期: 2020-03-04

基金资助

河南省高等学校重点科研（No.20A150039）资助项目.

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Construction of 3,4-Disubstituted-3-(difluoromethyl)pyrazoles

  • Zeng Junliang ,
  • Xu Zhihong ,
  • Ma Junan
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  • a School of Chemistry and Chemical Engineering, Xuchang University, Henan 461000;
    b Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Center of Chemical Science & Engineering, Department of Chemistry, Tianjin University, Tianjin 300072

Received date: 2019-12-18

  Revised date: 2020-02-03

  Online published: 2020-03-04

Supported by

Project supported by the Key Project of Education Department of Henan Province (Nos. 20A150039).

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摘要

二氟甲基在活性分子中可以起到氢键供体、生物电子等排体、亲脂性调节等作用，在药物和农药分子的设计中被广泛使用.3，4-二取代-3-（二氟甲基）吡唑骨架的发现及应用是该领域的一个突出代表，研究表明含有这类骨架的分子能够抑制琥珀酸脱氢酶（SDHIs），具有作为杀菌剂的潜力，目前市场上已有近十种农药分子含有3，4-二取代-3-（二氟甲基）吡唑结构单元，年销售额高达十几亿美元.按照所用含氟砌块的不同种类，对近二十年来3，4-二取代-3-（二氟甲基）吡唑类化合物的合成方法进行总结和展望.

关键词： 3,4-二取代-3-(二氟甲基)吡唑; 二氟甲基杂环化合物; 杀菌剂; 合成

本文引用格式

曾俊良 , 许志红 , 马军安 . 3,4-二取代-3-(二氟甲基)吡唑类化合物的构建[J]. 有机化学, 2020 , 40(5) : 1105 -1116 . DOI: 10.6023/cjoc201912024

Abstract

The CHF2 moiety has been widely utilized in the design of pharmaceuticals and agrochemicals, because this group can act as hydrogen-bonding donor to improve the binding selectivity of biologically active compounds, as a bioisostere to substitute for methyl, methoxy, hydroxy, amino and thiol groups, and as a lipophilic regulator to improve the liposolubility of the active compounds. For example, 3-difluoromethylpyrazole scaffolds are present in many organic compounds that exhibit important biological activities. In this content, there are nearly ten kinds of pesticide molecules on the market that contain 3,4-disubstituted-3-(difluoromethyl)pyrazole units, with annual sales of up to one billion dollars. In this review, the methods of construction of 3,4-disubstituted 3-difluoromethylpyrazoles will been briefly summarized that have been reported so far. Four different strategies including using fluorinated reagents as substrates, difluoroacetic acid and its derivatives as fluorine building blocks, difluorodiazonium and others as fluorine building blocks will be introduced.

Key words： 3,4-disubstituted-3-difluoromethylpyrazoles; difluoromethyl heterocyclic compounds; fungicides; synthesis

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