应用化学 ›› 2017, Vol. 34 ›› Issue (2): 146-150.DOI: 10.11944/j.issn.1000-0518.2017.02.160163

• 研究论文 • 上一篇    下一篇

6,6'-二甲基-2,2'-联吡啶-4,4'-二甲酸甲酯的合成与表征

柴永真a,常宇b,宋蕊琴a,刘巍a,李云辉a*(),潘利华b*()   

  1. a长春理工大学化学与环境工程学院 长春 130022
    b中国科学院长春应用化学研究所 长春 130022
  • 收稿日期:2016-04-15 接受日期:2016-07-05 出版日期:2017-01-18 发布日期:2017-01-18
  • 通讯作者: 李云辉,潘利华
  • 基金资助:
    吉林省重点科技攻关项目(批准号20150204010YY)吉林省发改委项目(批准号2014Y115)

Synthesis and Characterization of Dimethyl 6,6'-Dimethyl-[2,2'-bipyridine]-4,4'-dicarboxylate

CHAI Yongzhena,CHANG Yub,SONG Ruiqina,LIU Weia,LI Yunhuia*(),PAN Lihuab*()   

  1. aCollege of Chemical and Environmental Engineering,Changchun University of Science and Technology,Changchun 130022,China
    bChangchun Institute of Applied Chemistry,Chinese Academy of Sciences,Changchun 130022,China
  • Received:2016-04-15 Accepted:2016-07-05 Published:2017-01-18 Online:2017-01-18
  • Contact: LI Yunhui,PAN Lihua
  • Supported by:
    Supported by the Key Science and Technology Project of Jilin Province(No.20150204010YY), the Project of Jilin Provincial Development and Reform Commission(No.2014Y115)

摘要:

以6-甲基-2-羟基吡啶-4-甲酸甲酯为起始原料,经酯化反应制备2-甲基-6-(对甲苯磺酰氧基)吡啶-4-甲酸甲酯,使其在过渡金属镍络合物催化作用下自身偶联合成6,6'-二甲基-2,2'-联吡啶-4,4'-二甲酸甲酯,通过改变投料比例、反应温度及投料顺序获得最佳反应条件,收率77%。 经核磁共振、红外光谱、质谱及差示扫描热量法等对分子结构进行了表征,验证了合成方法的可靠性。 该结构能够满足均相时间分辨荧光免疫分析螯合剂中间体的需求。 目前,它已成功用于均相时间分辨荧光免疫分析。

关键词: 均相时间分辨荧光免疫分析, 自身偶联, 二甲基-联吡啶-二甲酸甲酯

Abstract:

Dimethyl 6,6'-dimethyl-[2,2'-bipyridine]-4,4'-dicarboxylate was synthesized in two steps from methyl 6-methyl-2-hydroxypyridine-4-carboxylate. The first step was the preparation of methyl 2-methyl-6-[(p-toluenesulfonyl)oxy]pyridine-4-carboxylate by esterification. The second step was to prepare the target product by nickel complex catalyzed homocoupling reaction. Several other factors which affected the reaction such as material proportion, reaction temperature and addition order were investigated. When the reaction was carried out under the optimal conditions, 77% yield was achieved. The products were characterized by nuclear magnetic resonance(NMR), Fourier transform infrared spectrometer(FTIR), mass spectrometry(MS) and differential scanning calorimetry(DSC) to prove the reliability of the synthetic method. This structure can fully satisfy the need of chelating agent intermediate for homogeneous time-resolved fluoroimmunoassay(HTRF), which has been succeeded in prectical applications.

Key words: homogeneous time-resolved fluoroimmunoassay, homocoupling, dimethyl dimethyl-[bipyridine]-dicarboxylate