对金属离子具有荧光选择识别作用的4-甲醛肟基苯甲酸乙酯的合成  

Synthesis of 4-(Hydroxyimino-methyl)Benzoic Acid Ethyl Ester with Fluorescence Selection Recognition to Selected Metal Ions

作　　者：于孟 万芳[1] 王勇[1] YU Meng;WAN Fang;WANG Yong(Hubei Key Laboratory of Drug Synthesis and Optimization,Jingchu University of Technology,Jingmen 444800,China)

机构地区：[1]荆楚理工学院药物合成与优化湖北省重点实验室,湖北荆门448000

出　　处：《化学试剂》2020年第5期572-577,共6页Chemical Reagents

基　　金：湖北省教育厅科学技术研究项目(Q20174302,Q20194301);荆楚理工学院培育项目(PY201901)。

摘　　要：以4-溴苯甲酸为原料,将其与二氯亚砜在乙醇溶液中回流反应制得4-溴苯甲酸乙酯。将4-溴苯甲酸乙酯与氰化亚铜反应制得4-氰基苯甲酸乙酯,将4-氰基苯甲酸乙酯与盐酸羟胺在碱性条件下反应得到白色固体目标化合物。对化合物进行IR、1HNMR和13CNMR等结构表征确证。合成路线具有操作简单、反应条件温和、生产成本低、产率高等优点。金属离子对目标化合物的荧光响应研究表明,其对Cu(Ⅱ)、Fe(Ⅲ)和Pb(Ⅱ)有很好的选择性。随着金属离子Cu(Ⅱ)、Fe(Ⅲ)和Pb(Ⅱ)的加入,目标化合物的荧光强度逐渐降低至基本消失。对于Mn(Ⅱ)、Fe(Ⅱ)、Cd(Ⅱ)、Ni(Ⅱ)、Zn(Ⅱ)和Cr(Ⅲ)等离子,随着金属离子的加入,目标化合物的荧光强度改变甚微或不改变。4-Bromobenzoic acid was used as a raw material,and it was refluxed with thionyl chloride in ethanol solution to obtain 4-bromo benzoic acid ethyl ester.Reaction of 4-bromo benzoic acid ethyl ester with cuprous cyanide afforded 4-cyano benzoic acid ethyl ester.The target compound,a white solid,was obtained by reaction of 4-cyano benzoic acid ethyl ester with hydroxylamine hydrochloride under basic condition.The compounds was structurally confirmed by IR,1HNMR and 13CNMR.The synthetic route has the advantages of simple operation,mild reaction conditions,low production cost and high yield.The fluorescence spectroscopy indicates that the target compound has a good selectivity for Cu(Ⅱ),Fe(Ⅲ)and Pb(Ⅱ)ions.With the addition of the metal ions Cu(Ⅱ),Fe(Ⅲ)and Pb(Ⅱ),the fluorescence intensity of the target compound gradually decreased to substantially disappear.For the Mn(Ⅱ),Fe(Ⅱ),Cd(Ⅱ),Ni(Ⅱ),Zn(Ⅱ)and Cr(Ⅲ)ions,the fluorescence intensity of the compound changes little or no change with the addition of metal ions.

关 键 词：荧光光谱 肟基 Cu(Ⅱ)离子 合成 结构表征 

分 类 号：O621.3[理学—有机化学]