肉桂酸及其衍生物的合成研究

发布时间：2018-04-19 06:29

本文选题：肉桂酸 + 衍生物　；参考：《合肥工业大学》2016年硕士论文

【摘要】：肉桂酸和它的衍生物在食品、医药、日化等方面有着重要的应用,同时肉桂酸在精细有机合成中也是非常重要的中间体。肉桂酸可以通过分子结构设计,苯环上引入羟基、甲氧基、硝基等基团;羧基进行酯化反应或酰化反应形成酯类、酰卤类、酰胺类衍生物。在此基础上,本文合成了一系列化合物,如肉桂酸、p-羟基肉桂酸、p-甲氧基肉桂酸、肉桂酰甘氨酸、p-甲氧基肉桂酰丙氨酸,并对以上化合物的合成及反应机理进行了探讨。(1)以苯甲醛和乙酸酐为原料,碳酸钾为催化剂经Perkin反应合成了肉桂酸,并确定了较适宜的合成条件,产率为56.1%。采用傅里叶红外光谱仪(Fourier Transform Infrared Spectrometer)、超导核磁共振波谱仪(Superconducting Nucleus Magnetic Resonance Spectrometer)和显微熔点仪对产物进行了结构表征。(2)分别在微波辐射和常规加热条件下,以p-羟基苯甲醛和乙酸酐为原料,碳酸钾为催化剂经Perkin反应合成了p-羟基肉桂酸,优化条件下产率达到71.9%。同时,探讨了不同的加热方法对p-羟基肉桂酸合成的影响。采用傅里叶红外光谱仪(FT-IR) 、超导核磁共振波谱仪('H NMR)和显微熔点仪对产物进行了结构表征。(3)以p-甲氧基苯甲醛和乙酸酐为原料,碳酸钾为催化剂经Perkin反应合成了p-甲氧基肉桂酸,优化条件下产率达39.7%。采用傅里叶红外光谱仪(FT-IR)、超导核磁共振波谱仪(1HNMR)和显微熔点仪对产物进行了结构表征。(4)以取代肉桂酸(自制)、氯化亚砜为原料,合成取代肉桂酰氯,然后取代肉桂酰氯再与氨基酸(甘氨酸、DL-丙氨酸)反应,以三聚磷酸钠作缚酸剂,合成了肉桂酰甘氨酸和p-甲氧基肉桂酰丙氨酸。以肉桂酰甘氨酸的合成为例,获得了较佳的合成反应条件,产率分别为75.3%和74.3%。采用傅里叶红外光谱仪(FT-IR)、超导核磁共振波谱仪(1H NMR, 13C NMR)对产物进行了分析表征并确认了产物的结构。
[Abstract]:Cinnamic acid and its derivatives have important applications in food, medicine, daily chemistry and so on. Meanwhile, cinnamic acid is also a very important intermediate in fine organic synthesis.Cinnamic acid can be designed by molecular structure, hydroxyl, methoxy and nitro groups are introduced into benzene ring and carboxyl groups are esterified or acylated to form esters, acyl halides and amides.On this basis, a series of compounds were synthesized, such as cinnamic acid p- hydroxycinnamic acid, cinnamyl glycine, cinnamyl cinnamyl alanine.The synthesis and reaction mechanism of above compounds were discussed. The cinnamic acid was synthesized by Perkin reaction with benzaldehyde and acetic anhydride as raw materials and potassium carbonate as catalyst. The optimum synthetic conditions were determined and the yield was 56.1%.The products were characterized by Fourier Transform Infrared spectrometerium, superconducting Nucleus Magnetic Resonance spectrometer and melting point spectrometer. The products were characterized by microwave radiation and conventional heating, respectively, using p-hydroxybenzaldehyde and acetic anhydride as raw materials.P-hydroxycinnamic acid was synthesized by Perkin reaction with potassium carbonate as catalyst, and the yield of p-hydroxycinnamic acid was 71.9 under the optimum conditions.At the same time, the effects of different heating methods on the synthesis of p-hydroxycinnamic acid were discussed.The structure of the product was characterized by Fourier transform infrared spectroscopy (FTIR), superconducting nuclear magnetic resonance spectroscopy (NMR) and melting point analyzer (FT-IR). The products were characterized using p-methoxybenzaldehyde and acetic anhydride as raw materials.P-methoxy cinnamic acid was synthesized by Perkin reaction with potassium carbonate as catalyst, and the yield was 39.7% under the optimum conditions.The products were characterized by Fourier transform infrared spectroscopy (FTIR), superconducting nuclear magnetic resonance spectroscopy (1HNMRs) and melting point spectrometer (FT-IR) to replace cinnamic acid (self-made cinnamic acid and sulfoxide chloride as raw material) to synthesize substituted cinnamyl chloride.Then substituted cinnamyl chloride reacted with amino acid (glycine DL-alanine) to synthesize cinnamyl glycine and pmethoxy cinnamyl alanine with sodium tripolyphosphate as acid binding agent.Taking the synthesis of cinnamyl glycine as an example, the optimum synthetic conditions were obtained. The yields were 75.3% and 74.3%, respectively.The products were characterized by Fourier transform infrared spectroscopy (FTIR) and superconducting nuclear magnetic resonance spectroscopy (1H-NMRs, 13C-NMRs). The structure of the products was confirmed.
【学位授予单位】：合肥工业大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O621.3

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