酸性离子液体催化加成及串联反应研究
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摘要
随着人们环保意识的增强,绿色化学成为研究的热点。酸性离子液体由于其本身独特的物理和化学性质在近年来得到广泛应用,成为绿色化学的一种重要途径。Lewis酸性离子液体、Bronsted酸性离子液体和固载型酸性离子液体的制备以及其在绿色合成中取得的重要成果,极大地拓展了酸性离子液体在化学化工领域中的应用。
论文发现了酸性离子液体室温高效催化oxa-Michael加成反应的新活性,研究发现酸性离子液体能够催化醇、苄基氨基醇类化合物与丁烯酮、丙烯醛之间的oxa-Michael加成反应。考察了离子液体的阴阳离子、离子液体的量、反应温度、底物比例、反应时间、底物结构对oxa-Michael加成反应的影响。实验结果表明,与传统的有机酸和咪唑类酸性离子液体催化的结果相比,所设计制备的酰胺类酸性离子液体具有更好的催化性能。提出了酰胺类酸性离子液体催化oxa-Michael加成反应的机理,并通过实验对该机理进行验证。
论文研究了酸性离子液体催化酚类化合物选择性加成反应的新功能。研究了酸性离子液体催化酚类化合物与丁烯酮、丙烯醛以及丙烯腈之间的加成反应,考察了离子液体类型、离子液体的量、反应温度、底物比例、反应时间和取代基对加成反应的影响。比较中性离子液体和酸性离子液体的催化差异后发现,在酸性离子液体中,酚类化合物能够发生可控选择性加成反应；而在中性离子液体中,酚类化合物不能够发生可控选择性加成反应。实验结果表明,取代基的性质和位置对于酚类化合物发生加成反应的化学选择性和区域选择性有重要的影响。在实验的基础上,提出了酸性离子液体催化酚类化合物选择性加成反应的可能机理。
论文探索了酸性离子液体催化串联反应合成四氢喹啉化合物的新途径。研究了酸性离子液体催化苯基氨基醇类化合物与丁烯酮、乙基乙烯基酮之间的串联反应,考察了离子液体类型、离子液体的量、反应温度、底物比例、反应时间、底物结构、有机溶剂对合成四氢喹啉化合物反应的影响。实验结果表明,酸性离子液体和三氯甲烷组成的两相体系具有更好的催化效果。在此条件下,一系列结构新颖的四氢喹啉化合物被合成。提出了酸性离子液体催化合成四氢喹啉化合物的串联反应历程,并通过实验对该历程进行验证。
论文总共合成了64种化合物,其中13种离子液体、18种oxa-Michael加成产物、9种C-加成产物、7种O-加成产物、8种苯基氨基醇化合物、6种四氢喹啉化合物以及3种N-成产物,产物经过1H NMR、13C NMR、FTIR、HRMS等手段表征分析和验证,其中30种为新化合物。
Recent years, the research of green chemistry is a hot topic due to the strengthening environmental consciousness. Acidic ionic liquid is an important synthetic route of green chemistry due to their unique physical and chemical properties. The preparation and development of Lewis acidic ionic liquid, Bronsted acidic ionic liquid and supported acidic ionic liquids widened the application of acidic ionic liquid in organic synthesis.
Acidic ionic liquid was found to catalyze the oxa-Michael addition reaction for the first time. The experimental results demonstrated that various alcohols proceeded smoothly with methyl vinyl ketone and acrylaldehyde, furthermore, O-selectivity addition of 2-(benzylamino)ethanol was also achieved. The effect of anions and cations, amount of ionic liquid, temperature, ratio, time and the structures of alcohols on the reaction was investigated. Comparing with traditional acidic imidazolium ionic liquids and organic acids, amides-based acidic ionic liquids gave the better results. Based on the results, a mechanism was postulated and the evidence for the role of amides-based acidic ionic liquids in promoting the oxa-Michael addition reaction had been given.
Acidic ionic liquid was firstly found to catalyze the selective addition of hydroxybenzenes. The selective addition reaction of various hydroxybenzenes with methyl vinyl ketone, acrylaldehyde and acrylonitrile proceeded smoothly. The effect of anions and cations, amount of ionic liquid, temperature, ratio, time and substituents on the reaction was investigated. The results demonstrated that the position and nature of substituent had important influence on the selectivity of addition. Based on the results, the possible mechanism of selective addition catalyzed by acidic ionic liquids had been given.
The synthesis of 1,2,3,4-tetrahydroquinoline derivatives catalyzed by acidic ionic liquid was explored. The influences of anions and cations, amount of ionic liquid, temperature, ratio, time, solvent on the reaction was investigated. Comparing with the result in acidic ionic liquid, the better result could be obtained in acidic ionic liquid/CH3Cl and a series of novel 1,2,3,4-tetrahydroquinoline compounds were synthesized. Based on the results, a possible process of the cascade reaction was postulated and the evidence had been given.
In the thesis,64 compounds were synthesized including 13 ionic liquids,18 oxa-Michael adducts,9 C-alkylated products,7 O-alkylated products,8 2-(phenylamino)ethanol derivatives,6 1,2,3,4-tetrahydroquinoline derivatives and 3 N-adducts. These compounds were characterized by 1H NMR,13C NMR, FTIR, HRMS and 30 compounds have been confirmed to be new compounds.
论文发现了酸性离子液体室温高效催化oxa-Michael加成反应的新活性,研究发现酸性离子液体能够催化醇、苄基氨基醇类化合物与丁烯酮、丙烯醛之间的oxa-Michael加成反应。考察了离子液体的阴阳离子、离子液体的量、反应温度、底物比例、反应时间、底物结构对oxa-Michael加成反应的影响。实验结果表明,与传统的有机酸和咪唑类酸性离子液体催化的结果相比,所设计制备的酰胺类酸性离子液体具有更好的催化性能。提出了酰胺类酸性离子液体催化oxa-Michael加成反应的机理,并通过实验对该机理进行验证。
论文研究了酸性离子液体催化酚类化合物选择性加成反应的新功能。研究了酸性离子液体催化酚类化合物与丁烯酮、丙烯醛以及丙烯腈之间的加成反应,考察了离子液体类型、离子液体的量、反应温度、底物比例、反应时间和取代基对加成反应的影响。比较中性离子液体和酸性离子液体的催化差异后发现,在酸性离子液体中,酚类化合物能够发生可控选择性加成反应；而在中性离子液体中,酚类化合物不能够发生可控选择性加成反应。实验结果表明,取代基的性质和位置对于酚类化合物发生加成反应的化学选择性和区域选择性有重要的影响。在实验的基础上,提出了酸性离子液体催化酚类化合物选择性加成反应的可能机理。
论文探索了酸性离子液体催化串联反应合成四氢喹啉化合物的新途径。研究了酸性离子液体催化苯基氨基醇类化合物与丁烯酮、乙基乙烯基酮之间的串联反应,考察了离子液体类型、离子液体的量、反应温度、底物比例、反应时间、底物结构、有机溶剂对合成四氢喹啉化合物反应的影响。实验结果表明,酸性离子液体和三氯甲烷组成的两相体系具有更好的催化效果。在此条件下,一系列结构新颖的四氢喹啉化合物被合成。提出了酸性离子液体催化合成四氢喹啉化合物的串联反应历程,并通过实验对该历程进行验证。
论文总共合成了64种化合物,其中13种离子液体、18种oxa-Michael加成产物、9种C-加成产物、7种O-加成产物、8种苯基氨基醇化合物、6种四氢喹啉化合物以及3种N-成产物,产物经过1H NMR、13C NMR、FTIR、HRMS等手段表征分析和验证,其中30种为新化合物。
Recent years, the research of green chemistry is a hot topic due to the strengthening environmental consciousness. Acidic ionic liquid is an important synthetic route of green chemistry due to their unique physical and chemical properties. The preparation and development of Lewis acidic ionic liquid, Bronsted acidic ionic liquid and supported acidic ionic liquids widened the application of acidic ionic liquid in organic synthesis.
Acidic ionic liquid was found to catalyze the oxa-Michael addition reaction for the first time. The experimental results demonstrated that various alcohols proceeded smoothly with methyl vinyl ketone and acrylaldehyde, furthermore, O-selectivity addition of 2-(benzylamino)ethanol was also achieved. The effect of anions and cations, amount of ionic liquid, temperature, ratio, time and the structures of alcohols on the reaction was investigated. Comparing with traditional acidic imidazolium ionic liquids and organic acids, amides-based acidic ionic liquids gave the better results. Based on the results, a mechanism was postulated and the evidence for the role of amides-based acidic ionic liquids in promoting the oxa-Michael addition reaction had been given.
Acidic ionic liquid was firstly found to catalyze the selective addition of hydroxybenzenes. The selective addition reaction of various hydroxybenzenes with methyl vinyl ketone, acrylaldehyde and acrylonitrile proceeded smoothly. The effect of anions and cations, amount of ionic liquid, temperature, ratio, time and substituents on the reaction was investigated. The results demonstrated that the position and nature of substituent had important influence on the selectivity of addition. Based on the results, the possible mechanism of selective addition catalyzed by acidic ionic liquids had been given.
The synthesis of 1,2,3,4-tetrahydroquinoline derivatives catalyzed by acidic ionic liquid was explored. The influences of anions and cations, amount of ionic liquid, temperature, ratio, time, solvent on the reaction was investigated. Comparing with the result in acidic ionic liquid, the better result could be obtained in acidic ionic liquid/CH3Cl and a series of novel 1,2,3,4-tetrahydroquinoline compounds were synthesized. Based on the results, a possible process of the cascade reaction was postulated and the evidence had been given.
In the thesis,64 compounds were synthesized including 13 ionic liquids,18 oxa-Michael adducts,9 C-alkylated products,7 O-alkylated products,8 2-(phenylamino)ethanol derivatives,6 1,2,3,4-tetrahydroquinoline derivatives and 3 N-adducts. These compounds were characterized by 1H NMR,13C NMR, FTIR, HRMS and 30 compounds have been confirmed to be new compounds.
引文
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