新型含吡唑香豆素结构的羟胺类荧光探针的合成及其在醛类化合物检测中的应用  

Synthesis of Novel Fluorescent Probes Containing Pyrazole-coumarinyl Hydroxylamine Structure and Its Application in the Detection of Aldehydes

作　　者：朱灏 张文清 杜传元 朱芳芳 胡晓松 刘亚群 ZHU Hao;ZHANG Wen-qing;DU Chuan-yuan;ZHU Fang-fang;HU Xiao-song;LIU Ya-qun(School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan, 430070, China)

机构地区：[1]武汉理工大学化学化工与生命科学学院,湖北武汉430070

出　　处：《合成化学》2022年第3期184-193,共10页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金面上项目(21472144);武汉理工大学自主创新研究基金资助项目(2020-IB-026,2021-IA-003);国家级大学生创新创业训练计划(202010497026)。

摘　　要：醛类化合物对人体健康和人类的生活质量有重要影响,开发高效、便捷的醛类物质检测方式有较强的现实意义。通过香豆素-悉尼酮与炔基化合物的点击反应,设计并合成了两种新型的含吡唑香豆素结构的羟胺类荧光探针(O-取代型和N-取代型),其结构经^(1)H NMR,^(13)C NMR,IR及HR-MS表征。其中,N-取代型羟胺探针可与食品中3种常见的糠醛类化合物(糠醛、5-甲基糠醛和5-羟甲基糠醛)进行荧光衍生反应。采用高效液相色谱-荧光检测和高分辨质谱对反应进行了分析。结果表明:衍生产物具有良好的色谱学行为,以及较高的荧光强度和较强的质谱峰信号。Aldehydes play an essential role in human health and quality of life.It is of great significance to develop efficient and convenient detection methods for aldehydes.This study designed and synthesized two novel fluorescent probes(O-substituted and N-substituted)containing pyrazole coumarinyl hydroxylamine structure through the click reaction between coumarin-sydnone and alkynyl compounds.The structures were confirmed by ^(1)H NMR,^(13)C NMR,IR and HR-MS.The N-substituted hydroxylamine was used in the fluorescent derivatization of three common furfural compounds(furfural,5-methylfurfural,5-hydroxymethylfurfural)in food,and the corresponding derivatives were analyzed by high-performance liquid chromatography coupled with fluorescence detection and high-resolution mass spectrometry.The results show that the derivates have good chromatographic behavior,high fluorescence intensity and strong mass spectrum peak signal.Therefore,the probe is expected to find extensive applications in the qualitative and quantitative analysis of aldehydes in various matrices.

关 键 词：醛类检测 点击反应 吡唑香豆素 羟胺 荧光探针 合成 糠醛 

分 类 号：O621.3[理学—有机化学] O657.3[理学—化学]