1-羟基-2,5,8-三甲基-9-芴酮的合成研究  

Synthesis of 1-hydroxy-2,5,8-trimethyl-9-fluorenone

作　　者：刘莉 杨瑞昆 蒋红霞 陈雪 刘建群 LIU Li;YANG Rui-kun;JIANG Hong-xia;CHEN Xue;LIU Jian-qun(Key Laboratory of Modern Preparation of TCM,Ministry of Education,Jiangxi University of Traditional Chinese Medicine,Jiangxi Nanchang 330004,China)

机构地区：[1]江西中医药大学现代中药制剂教育部重点实验室,江西南昌330004

出　　处：《广州化工》2021年第13期44-46,共3页GuangZhou Chemical Industry

基　　金：国家自然科学基金项目(81860686);江西省主要学科学术和技术带头人项目(20182BCB22004)。

摘　　要：1-羟基-2,5,8-三甲基-9-芴酮为雷公藤抗炎活性成分。以3-甲基水杨酸和对二甲苯为原料,醋酸钯为催化剂,过硫酸钠为氧化剂,经钯催化sp^(2) C-H氧化偶联一锅法,首次合成了目标物,通过NMR和MS进行了结构表征。正交实验和单因素实验表明,反应时间影响最大,其次是钯催化剂用量,第三是反应温度,最后是原料摩尔比,优化条件为:3-甲基乙酰水杨酸:对二甲苯:醋酸钯摩尔比=1:4:0.1、温度80℃、时间2 h,收率90.3%,纯度99.6%。1-hydroxy-2,5,8-trimethyl-9-fluorenone is an anti-inflammatory active compound from Tripterygium wilfordii.Using 2-hydroxy-3-methylbenzoic acid and p-xylene as raw materials,palladium acetate as catalyst,sodium persulfate as oxidant,1-hydroxy-2,5,8-trimethyl-9-fluorenone was synthesized by Pd-catalysed sp^(2) C-H oxidative coupling reaction,one-pot formation for the first time.Its structure was characterized by NMR and MS analysis.The orthogonal experiment and single factor experiment results indicated that the order of influence of factors was reaction time,Palladium dosage,reaction temperature and molar ratio of raw materials.The optimal reaction conditions showed as follows:molar ratio of 2-hydroxy-3-methylbenzoic acid,p-xylene and Palladium acetate was 1:4:0.1,the reaction temperature was 80℃,reaction time was 2 h,yielding 90.3%desired product with 99.6%purity.

关 键 词：1-羟基-2 5 8-三甲基-9-芴酮 钯催化 sp^(2)C-H氧化偶联反应 一锅法合成 

分 类 号：R284.3[医药卫生—中药学]