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新型多溴代水杨醛及其Schiff碱配体的合成与表征

Synthesis and characterization of novel multi-brominated salicylaldehyde and its Schiff base ligand

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【作者】 刘海彬; 王梅;

【Author】 LIU Hai-bin1,2,WANG Mei2 (1.Department of Biomedical Science & Chemical Engineering,Liaoning Institute of Science and Technology,Benxi 117004,China;2.State Key Laboratory of Fine Chemicals,Dalian University of Technology(DUT),Dalian 116012,China)

【机构】 辽宁科技学院生物医药与化学工程学院; 大连理工大学精细化工国家重点实验室;

【摘要】 以芳基硼酸和3-溴-5-叔丁基水杨醛为原料,经Suzuki偶联反应分别得到3-苯基-5-叔丁基水杨醛和3-(4-甲基苯基)-5-叔丁基水杨醛。3-苯基-5-叔丁基水杨醛在溴化反应时,发现不同温度下反应结果不同:分别生成一溴代产物3-(4-溴苯基)-5-叔丁基水杨醛和二溴代产物3-(4-溴苯基)-5-溴水杨醛。在50℃下,3-(4-甲基苯基)-5-叔丁基水杨醛经溴化得到三溴代产物3-(4-甲基-3,5-二溴苯基)-5-溴水杨醛,再经过与(S)-缬氨醇缩合后得到手性Schiff碱配体。通过红外、高分辨质谱、核磁共振等手段对其结构进行了表征。

【Abstract】 3-Phenyl-5-butylsalicylaldehyde and 3-(4-methyl-phenyl)-5-butylsalicylaldehyde were synthesized through the Suzuki coupling reactions using arylboric acids and 3-bromo-5-butylsalicylaldehyde as the starting materials.The products 3-(4-bromophenyl)-5-butylsalicylaldehyde with one bromine atom and 3-(4-bromophenyl)-5-bromosalicylaldehyde with two bromine atoms were obtained while 3-phenyl-5-butylsalicylaldehyde was brominated at different temperatures.3-(4-Methyl-3,5-dibromophenyl)-5-bromosalicylaldehyde with three bromine atoms was prepared when 3-(4-methylphenyl)-5-butylsalicylaldehyde was brominated at 50 ℃,then its chiral Schiff base ligand was obtained through condensation with(S)-valinol.The synthesized compounds were characterized by IR,HRMS,and NMR spectroscopy.

【基金】 国家自然科学基金资助项目(20471013、2063-3020)
  • 【分类号】O621.13
  • 【被引频次】10
  • 【下载频次】467
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