有机苯基亚膦酸酯衍生物新型反应研究
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摘要
二氯苯基膦(DCPP)是重要的化工中间体,它可衍生出许多化工产品。是合成各类芳香族有机膦化合物最重要的单体之一,也是制备农药,增塑剂,尼农稳定剂,染料,油漆配合物、消泡剂、抗氧剂、光聚物感光引发剂的中间体,具有广泛的用途。
研究发现,酰基氧化膦结构是目前最为重要的一类极具光化学反应活性的高性能光引发剂,在一定波长光的辐射下可以高效地以α形式断裂生成芳酰基-氧膦基自由基,近十几年来,国外对它的研究与应用颇为活跃,引起人们的广泛兴趣。作为高新性能光敏引发剂,广泛应用于光固涂料、光敏油墨、光刻胶、印刷电路板、液晶显示、汽车配件、光敏粘合剂、医疗器械、牙科材料、封装材料等领域。
α-氨基膦酸酯作为膦酰氨基酸的类似物,自20世纪50年代末从动物体内分离出来,因为其抗肿瘤,除草、植物生长调节、抑制酶活性及杀菌等重要的生物活性而受到众多科学家的关注。
α-细辛脑类化合物的偶联反应目前沿未见相关文献报道,本文利用中间体O-烷基苯基亚膦酸酯,醋酸钴,醋酸锰等催化剂首次催化α-细辛脑类化合物的自偶联反应。
本文综述了酰基氧化膦光引发剂及α-氨基膦酸酯的合成方法,以二氯苯基膦为原料经中间体O,O-二烷基苯基亚膦酸酯和O-烷基苯基亚膦酸酯合成了7个有机膦光引发剂, 8个尚未见文献报道的α-氨基苯基膦酸酯和2个尚未见文献报道的α-细辛脑类化合物(类茋类化合物)的自偶联产物。主要研究内容可分为以下三部分:
第一部分以氯苯为催化剂,苯基二氯化膦、均三甲基苯甲酰氯等为主要原料在金属钠的参与下合成双(2, 4, 6-三甲基苯甲酰基)苯基膦等,化合物6不需分离直接经双氧水或硫磺氧化得目标化合物双(2, 4, 6-三甲基苯甲酰基)苯基氧化膦或硫化膦等有机膦光引发剂。同时利用手中已有原料苯基二氯化膦先制得中间体O,O-二烷基苯基膦酸酯,随后通过Aubuzov反应合成了三种有机膦光引发剂.
第二部分以苯基二氯化膦为原料合成了O-烷基苯基亚膦酸酯,利用该中间体中的P-H键与芳香醛、芳香胺的类Mannich反应,一锅煮合成了一系列具有多种潜在生物活性的新型α-氨基苯基膦酸酯。
第三部分以O-烷基苯基亚膦酸酯、醋酸钴、醋酸锰为催化剂,研究了α-细辛脑类化合物(类茋类化合物)的自偶联反应,并推测出其可能的反应机理。
本论文共合成化合物22个,其中新化合物10个.用1H NMR、IR和MS对所合成的有机膦光引发剂及α-氨基膦酸酯衍生物进行了结构表征与确认,α-细辛脑类化合物(类茋类化合物)的自偶联产物单晶正在培养中。
Dichlorophenylphosphine is an important monomer of organophosphorus compound. It is also an intermediate to synthesize pesticides, plasticizer, nylon stabilizer, dye, paint adjuvant, anti-blowing agent, antioxidant, photopolymerization evocating agent.
It is discovered that the most important kind of mere initiator of high performance that has activity of photochemical reaction very much at present that acyl base oxidizes phosphine structure, can produce sweet-smelling acyl base - oxygen phosphine base free radical under certain radiation mere in wavelength by rupturing in the form ofαhigh-efficiently, in recent ten years, the study and application of it is rather active abroad, cause people's extensive interest.. An additional advantage is the disappearance of the yellow hue upon curing, As photosensitive initiator of high-new performance, apply to the mere firm coating extensively, photosensitive printing ink, photoengraving glue, printed circuit board, liquid crystal reveal, the car fittings, photosensitive binder, medical equipment, dentistry materialing, encapsulating fields such as materials,etc..
As the analogues of phosphoryl amino acids, a-amino phosphonates and their derivates have attracted many researchers' attentions for they are antitumor, herbicides, antibiotics and enzyme inhibitors since they were found in the animal body.
In this paper, recent advance in method, synthesis and of acylphophine photonitiators and a-amino phosphonates. 7 compounds of acylphosphine oxides photoinitiators, 8 compounds of a-amino phosphonates esters which not reported in literatures are synthesized from dicholophenylphosphine and 2 coupled compounds viaα-asarone which not reported in literatures. Three major sections are involved in this thesis.
In the first section, some acylphophine photoinitiators were synthesized by one-pot of dichlorophenylphosphine 2,4,6-trimethylbenzoly halide alkali metal and dihydrogen oxide. the reaction is preferable carried out in the presence of catalyst, preferable chlorobenzene. At the same time, 3 compounds of acylphophine photoinitiators were synthesized by Aubuzov condensation reaction of 2,4,6-trimethylbenzoly halide and O-dialkylphenylphosphite ester which was prepared from dichlrophenyl phosphine.
In the second section, a series ofα-aminophenylphosphonates, which present potential wide biological activities, were synthesized by one-pot Mannich-based condensation reaction of aryl aldehydes, aryl amines and phenylphosphite ester which contains P-H bond and was prepared from dichlorophenyl phosphine, the described process is a simple and reliable to synthesize target compounds in good yield. Their structures were confirmed by FT-IR,1H NMR and MS spectra.
In the third section, do some research about the coupling reaction ofα-asarone via O-alkylphenylphosphite ester, manganese acetate and cobaltous acetate, and discussed about the possibility mechanism.
We have synthesized 22 compounds, 10 of which not reported in literatures until now. Their structures were characterized and confirmed by IR, 1H NMR and MS spectra.
研究发现,酰基氧化膦结构是目前最为重要的一类极具光化学反应活性的高性能光引发剂,在一定波长光的辐射下可以高效地以α形式断裂生成芳酰基-氧膦基自由基,近十几年来,国外对它的研究与应用颇为活跃,引起人们的广泛兴趣。作为高新性能光敏引发剂,广泛应用于光固涂料、光敏油墨、光刻胶、印刷电路板、液晶显示、汽车配件、光敏粘合剂、医疗器械、牙科材料、封装材料等领域。
α-氨基膦酸酯作为膦酰氨基酸的类似物,自20世纪50年代末从动物体内分离出来,因为其抗肿瘤,除草、植物生长调节、抑制酶活性及杀菌等重要的生物活性而受到众多科学家的关注。
α-细辛脑类化合物的偶联反应目前沿未见相关文献报道,本文利用中间体O-烷基苯基亚膦酸酯,醋酸钴,醋酸锰等催化剂首次催化α-细辛脑类化合物的自偶联反应。
本文综述了酰基氧化膦光引发剂及α-氨基膦酸酯的合成方法,以二氯苯基膦为原料经中间体O,O-二烷基苯基亚膦酸酯和O-烷基苯基亚膦酸酯合成了7个有机膦光引发剂, 8个尚未见文献报道的α-氨基苯基膦酸酯和2个尚未见文献报道的α-细辛脑类化合物(类茋类化合物)的自偶联产物。主要研究内容可分为以下三部分:
第一部分以氯苯为催化剂,苯基二氯化膦、均三甲基苯甲酰氯等为主要原料在金属钠的参与下合成双(2, 4, 6-三甲基苯甲酰基)苯基膦等,化合物6不需分离直接经双氧水或硫磺氧化得目标化合物双(2, 4, 6-三甲基苯甲酰基)苯基氧化膦或硫化膦等有机膦光引发剂。同时利用手中已有原料苯基二氯化膦先制得中间体O,O-二烷基苯基膦酸酯,随后通过Aubuzov反应合成了三种有机膦光引发剂.
第二部分以苯基二氯化膦为原料合成了O-烷基苯基亚膦酸酯,利用该中间体中的P-H键与芳香醛、芳香胺的类Mannich反应,一锅煮合成了一系列具有多种潜在生物活性的新型α-氨基苯基膦酸酯。
第三部分以O-烷基苯基亚膦酸酯、醋酸钴、醋酸锰为催化剂,研究了α-细辛脑类化合物(类茋类化合物)的自偶联反应,并推测出其可能的反应机理。
本论文共合成化合物22个,其中新化合物10个.用1H NMR、IR和MS对所合成的有机膦光引发剂及α-氨基膦酸酯衍生物进行了结构表征与确认,α-细辛脑类化合物(类茋类化合物)的自偶联产物单晶正在培养中。
Dichlorophenylphosphine is an important monomer of organophosphorus compound. It is also an intermediate to synthesize pesticides, plasticizer, nylon stabilizer, dye, paint adjuvant, anti-blowing agent, antioxidant, photopolymerization evocating agent.
It is discovered that the most important kind of mere initiator of high performance that has activity of photochemical reaction very much at present that acyl base oxidizes phosphine structure, can produce sweet-smelling acyl base - oxygen phosphine base free radical under certain radiation mere in wavelength by rupturing in the form ofαhigh-efficiently, in recent ten years, the study and application of it is rather active abroad, cause people's extensive interest.. An additional advantage is the disappearance of the yellow hue upon curing, As photosensitive initiator of high-new performance, apply to the mere firm coating extensively, photosensitive printing ink, photoengraving glue, printed circuit board, liquid crystal reveal, the car fittings, photosensitive binder, medical equipment, dentistry materialing, encapsulating fields such as materials,etc..
As the analogues of phosphoryl amino acids, a-amino phosphonates and their derivates have attracted many researchers' attentions for they are antitumor, herbicides, antibiotics and enzyme inhibitors since they were found in the animal body.
In this paper, recent advance in method, synthesis and of acylphophine photonitiators and a-amino phosphonates. 7 compounds of acylphosphine oxides photoinitiators, 8 compounds of a-amino phosphonates esters which not reported in literatures are synthesized from dicholophenylphosphine and 2 coupled compounds viaα-asarone which not reported in literatures. Three major sections are involved in this thesis.
In the first section, some acylphophine photoinitiators were synthesized by one-pot of dichlorophenylphosphine 2,4,6-trimethylbenzoly halide alkali metal and dihydrogen oxide. the reaction is preferable carried out in the presence of catalyst, preferable chlorobenzene. At the same time, 3 compounds of acylphophine photoinitiators were synthesized by Aubuzov condensation reaction of 2,4,6-trimethylbenzoly halide and O-dialkylphenylphosphite ester which was prepared from dichlrophenyl phosphine.
In the second section, a series ofα-aminophenylphosphonates, which present potential wide biological activities, were synthesized by one-pot Mannich-based condensation reaction of aryl aldehydes, aryl amines and phenylphosphite ester which contains P-H bond and was prepared from dichlorophenyl phosphine, the described process is a simple and reliable to synthesize target compounds in good yield. Their structures were confirmed by FT-IR,1H NMR and MS spectra.
In the third section, do some research about the coupling reaction ofα-asarone via O-alkylphenylphosphite ester, manganese acetate and cobaltous acetate, and discussed about the possibility mechanism.
We have synthesized 22 compounds, 10 of which not reported in literatures until now. Their structures were characterized and confirmed by IR, 1H NMR and MS spectra.
引文
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