电化学氟化合成含氟药物中间体的基础研究
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摘要
氟是最活泼、电负性最强的非金属元素，将氟原子引入到有机物中会显著地改善它的物理和化学性质。药物中引入氟原子或含氟基团后，具有拟态效应、亲脂性和稳定性等一系列特殊的性质，从而导致含氟药物毒性降低、药效提高、代谢增强、药性持久，故广泛地应用于临床医学。有机物中引入氟原子的方法很多，但多数为污染较大、装置复杂、操作危险、且需要多步反应的化学氟化方法。电化学氟化方法作为新兴的氟化方法，可以在温和的条件下将氟原子直接引入到有机物中，具有很强的优势，倍受国内外学者关注。
电化学氟化通常分为全氟化和选择性氟化两大类。后者的研究领域目前更为活跃，但我国在这方面的研究刚刚起步。本论文运用电化学选择性氟化方法合成一系列含氟的氮杂环化合物，并对氟化机理进行了初步的探讨。具体研究内容如下：
对吡啶、咪唑和1,2,4-三唑成功地进行了电化学选择性氟化。并探讨了吡啶氟化的机理；
在自编程序辅助下，利用紫外光谱的加和性原理分析测定了含吡啶及其氟化物的混合样品；
为了考察不同基团对选择性电氟化的影响，合成了一系列含亚甲基的氮杂环化合物：1-(1H-咪唑-1-基)-苯乙酮,1-(1H-咪唑-5-基)-苯乙酮, 1-(1,2,4-三唑-1-基)-苯乙酮；
对已合成的亚甲基氮杂环化合物进行了初步的电化学选择性氟化研究。
Fluoro is the most vivacious, and the strongest electronegative of all nonmatal elements. When fluoro is imported into organic compounds, their chemical and physical properties can be significantly changed. The pharmaceutical has series of special properties such as mimesis effect, lipophilic effect and stability etc., which result in less toxicity, better metabolizability, longer pharmic effect and higher curative effect, when fluoro element or groups containing fluoro are imported into pharmaceutical. Although many methods of preparation of fluoroorganics have been developed to date, they often have unavoidable disadvantages such as complicated equipment, toxic reagents, hazardous operation, serious pollution, and multistep routs in chemical fluorination. Electrochemical fluorination, as a novel fluorination method, can import fluoro into organic compounds directly under mild conditions.
Electrochemical fluorination can be classified into two sorts: completely fluorination and selectively fluorination. The latter is more attractive, but in our country this research is just in earlier period. In this paper, we synthesize series of containing fluoro and nitrogen heterocycles compound with selectively electrochemical fluorination. Detailed research contents are as follows:
(1) Succeed in selectivity electrochemical fluorinating pyridine, imidazole and 1,2,4-triazole. And discuss the mechanism of selectivity electrochemical fluorination pyridine；
(2) Assisting by self-edit program, use adding theory of UV spectra analysis and determine admixture of pyridine and its fluoropyridine;
(3) In order to investigate the erect of different group on selectively fluorination, we synthesized series of containing nitrogen ethylene group compounds: 1-(1H-imidazole-1-yl)-acetophenone, 1-(1H- imidazole -5-yl)- acetophenone，1-(1,2,4-triazole-1-yl)- acetophenone；
(4) Primary research on selectivity electrochemical fluorination of the above-mentioned ethylene group compounds.
电化学氟化通常分为全氟化和选择性氟化两大类。后者的研究领域目前更为活跃，但我国在这方面的研究刚刚起步。本论文运用电化学选择性氟化方法合成一系列含氟的氮杂环化合物，并对氟化机理进行了初步的探讨。具体研究内容如下：
对吡啶、咪唑和1,2,4-三唑成功地进行了电化学选择性氟化。并探讨了吡啶氟化的机理；
在自编程序辅助下，利用紫外光谱的加和性原理分析测定了含吡啶及其氟化物的混合样品；
为了考察不同基团对选择性电氟化的影响，合成了一系列含亚甲基的氮杂环化合物：1-(1H-咪唑-1-基)-苯乙酮,1-(1H-咪唑-5-基)-苯乙酮, 1-(1,2,4-三唑-1-基)-苯乙酮；
对已合成的亚甲基氮杂环化合物进行了初步的电化学选择性氟化研究。
Fluoro is the most vivacious, and the strongest electronegative of all nonmatal elements. When fluoro is imported into organic compounds, their chemical and physical properties can be significantly changed. The pharmaceutical has series of special properties such as mimesis effect, lipophilic effect and stability etc., which result in less toxicity, better metabolizability, longer pharmic effect and higher curative effect, when fluoro element or groups containing fluoro are imported into pharmaceutical. Although many methods of preparation of fluoroorganics have been developed to date, they often have unavoidable disadvantages such as complicated equipment, toxic reagents, hazardous operation, serious pollution, and multistep routs in chemical fluorination. Electrochemical fluorination, as a novel fluorination method, can import fluoro into organic compounds directly under mild conditions.
Electrochemical fluorination can be classified into two sorts: completely fluorination and selectively fluorination. The latter is more attractive, but in our country this research is just in earlier period. In this paper, we synthesize series of containing fluoro and nitrogen heterocycles compound with selectively electrochemical fluorination. Detailed research contents are as follows:
(1) Succeed in selectivity electrochemical fluorinating pyridine, imidazole and 1,2,4-triazole. And discuss the mechanism of selectivity electrochemical fluorination pyridine；
(2) Assisting by self-edit program, use adding theory of UV spectra analysis and determine admixture of pyridine and its fluoropyridine;
(3) In order to investigate the erect of different group on selectively fluorination, we synthesized series of containing nitrogen ethylene group compounds: 1-(1H-imidazole-1-yl)-acetophenone, 1-(1H- imidazole -5-yl)- acetophenone，1-(1,2,4-triazole-1-yl)- acetophenone；
(4) Primary research on selectivity electrochemical fluorination of the above-mentioned ethylene group compounds.
引文
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