新型靛红衍生的对亚甲基苯醌的合成与表征
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摘要
为了在本科阶段加强对学生科研能力的培养,我们结合自身的科研工作和有机化学最新科研成果,介绍一个面向大学高年级本科生的综合性有机化学实验——新型靛红衍生的对亚甲基苯醌的合成与结构表征。以靛红为起始原料,经过脱水缩合、氨基上Boc保护基两步反应,结合柱层析、萃取等多种分离手段,最终得到目标化合物。实验中采用TLC法跟踪实验的反应进程,并利用熔点测定、红外光谱和核磁共振谱图等表征手段确定了目标化合物的结构。
In order to strengthen students' scientific research ability in the undergraduate stage, combined our own research work and the latest scientific research results of organic chemistry, a comprehensive organic chemistry experiment for senior undergraduates, the synthesis and characterization of a novel para-quinone methides derived from isatin, was introduced. Starting from isatins, after two-step reaction of dehydration condensation and introducing Boc protecting group on the amino group, combined chromatography, extraction and other separation methods, the target compound was finally obtained. TLC was used to track the progress of the experiment. The structure of the target compound was determined by melting point determination, infrared spectroscopy and nuclear magnetic resonance spectroscopy.
In order to strengthen students' scientific research ability in the undergraduate stage, combined our own research work and the latest scientific research results of organic chemistry, a comprehensive organic chemistry experiment for senior undergraduates, the synthesis and characterization of a novel para-quinone methides derived from isatin, was introduced. Starting from isatins, after two-step reaction of dehydration condensation and introducing Boc protecting group on the amino group, combined chromatography, extraction and other separation methods, the target compound was finally obtained. TLC was used to track the progress of the experiment. The structure of the target compound was determined by melting point determination, infrared spectroscopy and nuclear magnetic resonance spectroscopy.
引文
[1] 孔祥平,曲宝涵,吕海涛,等.基于应用型创新人才培养的实验教学模式研究[J].大学化学,2016,31(7):24-28.
[2] 李公春,孙婷,侯旭峰,等.有机化学实验教学改革的研究与实践[J].实验室科学,2011,143(3):38-40.
[3] 张颖,姜文清,贾定先.乙基叔丁基醚的绿色合成-推荐一个设计性综合化学实验[J].化学教育,2013,34(1):73-75.
[4] Zhou J,Bai,L J,Liang,G J,et al.Organocatalytic asymmetric domino Michael/O-alkylation reaction for the construction of succinimide substituted 3(2H)-furanones catalyzed by quinine[J].RSC Adv,2017,7(63):39885-39888.
[5] NagamineJ,Nagata R,Seki H,et al.Pharmacological profile of a new orally active growth hormone secretagogue,SM-130686[J].J.Endocrinol.,2001,171(3):481-489.
[6] Lin C,Shen Y Y,Huang B,et al.Synthesis of Amides and Nitriles from Vinyl Azides and p-Quinone Methides[J].J.Org.Chem.,2017,82(7):3950-3956.
[2] 李公春,孙婷,侯旭峰,等.有机化学实验教学改革的研究与实践[J].实验室科学,2011,143(3):38-40.
[3] 张颖,姜文清,贾定先.乙基叔丁基醚的绿色合成-推荐一个设计性综合化学实验[J].化学教育,2013,34(1):73-75.
[4] Zhou J,Bai,L J,Liang,G J,et al.Organocatalytic asymmetric domino Michael/O-alkylation reaction for the construction of succinimide substituted 3(2H)-furanones catalyzed by quinine[J].RSC Adv,2017,7(63):39885-39888.
[5] NagamineJ,Nagata R,Seki H,et al.Pharmacological profile of a new orally active growth hormone secretagogue,SM-130686[J].J.Endocrinol.,2001,171(3):481-489.
[6] Lin C,Shen Y Y,Huang B,et al.Synthesis of Amides and Nitriles from Vinyl Azides and p-Quinone Methides[J].J.Org.Chem.,2017,82(7):3950-3956.
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