“一锅煮”制备Biginelli和Hantzsch两种产物及其结构分析
|
摘要
苯甲醛、尿素和乙酰乙酸乙酯三组分"一锅煮"可以同时制备Biginelli和Hantzsch两种产物。教学中通过改变催化剂种类、反应物料比、反应溶剂等条件,引导学生探讨反应条件的改变对总产率及两种异构体比例的影响。实验中通过薄层色谱来跟踪反应进程,通过柱色谱分离混合物,最后通过熔点、红外光谱对合成的化合物进行结构表征。本实验集无机化学、有机化学、基础分析化学和仪器分析于一体,具有很强的实用性和可操作性,可作为有机化学实验中的综合性、设计性实验开设。
A new comprehensive and designing organic chemistry experiment is introduced.3,4-Dihydropyrimidinone(Biginelli product)and 1,4-dihydropyridine(Hantzsch product)are synthesized in one-pot of benzaldehyde,urea and ethyl acetoacetate under catalysts.Students are guided to explore the influence of reaction conditions,such as catalysts,material feeding ratio and solvents,on the total yield and the ratio of two isomers.The reaction is monitored by thin layer chromatographic.Biginelli and Hantzsch products are both simultaneously purified by column chromatography and characterized by melting point and IR spectrum.This experiment integrating inorganic,organic,fundamental analysis and instrument analysis,and has very strong practicability and maneuverability.It can be set up as a comprehensive and designing organic experiment.
A new comprehensive and designing organic chemistry experiment is introduced.3,4-Dihydropyrimidinone(Biginelli product)and 1,4-dihydropyridine(Hantzsch product)are synthesized in one-pot of benzaldehyde,urea and ethyl acetoacetate under catalysts.Students are guided to explore the influence of reaction conditions,such as catalysts,material feeding ratio and solvents,on the total yield and the ratio of two isomers.The reaction is monitored by thin layer chromatographic.Biginelli and Hantzsch products are both simultaneously purified by column chromatography and characterized by melting point and IR spectrum.This experiment integrating inorganic,organic,fundamental analysis and instrument analysis,and has very strong practicability and maneuverability.It can be set up as a comprehensive and designing organic experiment.
引文
[1]门吉英,赵林秀,王蕊欣,等.以开放式实验教学平台为基础提升制药工程专业学生的实践创新能力[J].化工高等教育,2017(1):59-62.
[2]王春玲,孙尔康.大学化学实验培养学生创新能力的探索[J].实验技术与管理,2011,28(10):27-30.
[3]李军,马占华,段红玲,等.“以学生为中心”的教学理念在化工原理课程设计教学中的实践[J].化工高等教育,2016(6):19-22.
[4]罗娅君,胡晓黎,李松,等.探索综合化学实验培养学生综合创新能力[J].实验室研究与探索,2011,30(II):100-102.
[5]冯清.问题引导下的探究式实验教学模式研究[J].实验技术与管理,2012,29(5):164-165.
[6]王书文,曹玮.综合性和创新性实验的设计与实践-Biginelli反应[J].实验室研究与探索,2007,26(1):100-102.
[7]曹玮,王书文.红外光谱在有机综合实验中的应用尝试[J].实验技术与管理,2007,24(2):41-43.
[8]Phillips,A P.Hantzsch's pyridine synthesis[J].Journal of the American Chemical Society,1949,71:4003-4007.
[9]Kappe,C O.100Years of the Biginellidihydropyrimidine synthesis[J].Tetrahedron,1993,49:6937-6963.
[10]李明,刘永军,王书文,等.有机化学实验[M].北京:科学出版社,2010:98-100,146-147,155-156,209-213.
[11]Li Ming,Guo Weisi,Wen Lirong.One-pot synthesis of Biginelli and Hantzsch products catalyzed by non-toxic ionic liquid(BMImSac)and structural determination of two products[J].Journal of Molecular Catalysis A:Chemical,2006,258:133-138.
[2]王春玲,孙尔康.大学化学实验培养学生创新能力的探索[J].实验技术与管理,2011,28(10):27-30.
[3]李军,马占华,段红玲,等.“以学生为中心”的教学理念在化工原理课程设计教学中的实践[J].化工高等教育,2016(6):19-22.
[4]罗娅君,胡晓黎,李松,等.探索综合化学实验培养学生综合创新能力[J].实验室研究与探索,2011,30(II):100-102.
[5]冯清.问题引导下的探究式实验教学模式研究[J].实验技术与管理,2012,29(5):164-165.
[6]王书文,曹玮.综合性和创新性实验的设计与实践-Biginelli反应[J].实验室研究与探索,2007,26(1):100-102.
[7]曹玮,王书文.红外光谱在有机综合实验中的应用尝试[J].实验技术与管理,2007,24(2):41-43.
[8]Phillips,A P.Hantzsch's pyridine synthesis[J].Journal of the American Chemical Society,1949,71:4003-4007.
[9]Kappe,C O.100Years of the Biginellidihydropyrimidine synthesis[J].Tetrahedron,1993,49:6937-6963.
[10]李明,刘永军,王书文,等.有机化学实验[M].北京:科学出版社,2010:98-100,146-147,155-156,209-213.
[11]Li Ming,Guo Weisi,Wen Lirong.One-pot synthesis of Biginelli and Hantzsch products catalyzed by non-toxic ionic liquid(BMImSac)and structural determination of two products[J].Journal of Molecular Catalysis A:Chemical,2006,258:133-138.