含吗啉基片段的水杨醛席夫碱类化合物的合成及其淬灭1,1-二苯基-2-三硝基苯肼自由基性能

doi:10.11944/j.issn.1000-0518.2019.05.180296

摘要/Abstract

摘要：

通过3-氟-4-吗啉基苯胺和取代水杨醛缩合反应,合成了14个含吗啉基片段水杨醛席夫碱类化合物(Ⅰa-Ⅰn)。通过核磁共振波谱仪(NMR)、傅里叶变换红外光谱仪(FTIR)、液相色谱-质谱联用仪(LC-MS)和元素分析等技术手段研究了产物的结构和淬灭1,1-二苯基-2-三硝基苯肼(DPPH)自由基的活性。结果表明,在0.02~0.10 g/L,所有化合物均表现出一定的淬灭DPPH自由基活性。其中,化合物Ⅰd和Ⅰf表现出较为优异的性能,化合物Ⅰd的活性在30%~55%,化合物Ⅰf的活性则大于50%。随着化合物Ⅰd、Ⅰh、Ⅰj和Ⅰn质量浓度的增大,其淬灭DPPH自由基的活性均呈现增强趋势。

关键词: 3-氟-4-吗啉基苯胺, 席夫碱, 1,1-二苯基-2-三硝基苯肼自由基

Abstract:

Fourteen kinds of salicylaldehyde Schiff bases containing morpholinyl fragments are synthesized by the condensation reaction of 3-fluoro-4-morpholiniline and substituted salicylate and confirmed by nuclear magnetic resonance spectroscopy(NMR), Fourier transform infrared spectrometer(FTIR), liquid chromatography-mass spectrometer(LC-MS) and element analysis. The 1,1-diphenyl-2-picrylhydrazyl(DPPH) radical quenching activities of these Schiff bases are also studied. The results show that all compounds show certain quenching activity of DPPH radicals at concentrations of 0.02 to 0.10 g/L. Among them, the compounds Ⅰd and Ⅰf show excellent properties. The activity of compound Ⅰd is between 30% and 55%, and the activity of compound Ⅰf is more than 50%. With the increase of the concentration of compounds Ⅰd, Ⅰh, Ⅰj and Ⅰn, the DPPH radical quenching activities increase.

Key words: 3-fluoro-4-morpholinine, Schiff base, 1,1-diphenyl-2-picrylhydrazyl radical

孙凤梅,韩琼,赵潘祥,王佳,芮佳怡,徐继明. 含吗啉基片段的水杨醛席夫碱类化合物的合成及其淬灭1,1-二苯基-2-三硝基苯肼自由基性能[J]. 应用化学, 2019, 36(5): 524-531.

SUN Fengmei,HAN Qiong,ZHAO Panxiang,WANG Jia,RUI Jiayi,XU Jiming. Synthesis and 1,1-Diphenyl-2-Picrylhydrazyl Radical Quenching Activity of Salicylaldehyde Schiff Bases Containing Morpholine Fragments[J]. Chinese Journal of Applied Chemistry, 2019, 36(5): 524-531.

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