2-溴丁酰氯与8-羟基喹诺酮在无水三氯化铝催化下的反应研究  

Study on the reaction of 2-bromobutyryl chloride and 8-hydroxyquinolone catalyzed by aluminum chloride

作　　者：段怡静 蔡林林 刘雨婷 罗贵琴 余镜瑶 钟柳 王启卫 刘治国 DUAN Yijing;CAI Linlin;LIU Yuting;LUO Guiqin;YU Jingyao;ZHONG Liu;WANG Qiwei;LIU Zhiguo(College of Science,Xihua University,Chengdu 610039,Sichuan,China;Yibin Key Laboratory of Small Molecule Chiral Chemical Drug Research and Application,Yibin 644002,Sichuan,China)

机构地区：[1]西华大学理学院,四川成都610039 [2]小分子手性化学药物研究与应用宜宾市重点实验室,四川宜宾644002

出　　处：《化学研究》2022年第3期209-213,共5页Chemical Research

基　　金：四川省科技重点项目(2020DYF1385)。

摘　　要：酰氯与酚在无水三氯化铝等路易斯酸催化下能顺利地进行傅-克反应,但是2-溴丁酰氯与8-羟基喹诺酮在无水三氯化铝催化下没有得到预期的目标化合物。利用核磁共振氢谱(^(1)H NMR)和液质联用(LC-MS)分析证明,在无水三氯化铝存在下,2-溴丁酰氯与8-羟基喹诺酮于-10~40℃反应主要生成酯化产物8-(2-溴丁酰氧基)喹诺酮以及少量氯取代溴的酯化物8-(2-氯丁酰氧基)喹诺酮。LC-MS分析表明,在反应温度70℃时,2-溴丁酰氯与8-羟基喹诺酮在无水三氯化铝存在下发生了傅-克反应,同时发生了消除一分子卤化氢的反应,生成了5-(2-丁烯酰基)-8-羟基喹诺酮和7-(2-丁烯酰基)-8-羟基喹诺酮为主的混合物。The Friedel-Crafts reaction of acyl chloride with phenol can be carried out smoothly under the catalysis of Lewis acid such as anhydrous aluminum chloride,but the expected target compound is not obtained between 2-bromobutyryl chloride and 8-hydroxyquinolone under the catalysis of anhydrous aluminum chloride.It was confirmed by ^(1)H NMR and LC-MS that at-10℃to 40℃,the reaction of 2-bromobutyryl chloride with 8-hydroxyquinolone mainly resulted in the formation of the esterified product 8-(2-bromobutyryloxy)quinolone,followed by a small amount of 8-(2-chlorobutyryloxy)quinolone,which was the esterification product of chloride substituted bromine.However,when the reaction of 2-bromobutyryl chloride with 8-hydroxyquinolone was conducted at 70℃,a mixture of 5-(2-butenoyl)-8-hydroxyquinolone and 7-(2-butenoyl)-8-hydroxyquinolone was formed.

关 键 词：8-羟基喹诺酮 8-(2-溴丁酰氧基)喹诺酮 2-溴丁酰氯 

分 类 号：O62[理学—有机化学]