6-氯-1,4-二氢-1,4-环氧萘的合成  

Synthesis of 6-chloro-1,4-dihydro-1,4-epoxynaphthalene

作　　者：徐小娜 王晓霞[1] 李祯[1] 柯苗 仝红娟 XU Xiao-na;WANG Xiao-xia;LI Zhen;KE Miao;TONG Hong-juan(School of Pharmaceutical&Chemical Engineering,Xianyang Vocational Technical College,Xianyang 712000,China;Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine in Shaanxi Province,School of Pharmacy,Shaanxi Institute of International Trade&Commerce,Xi'an 712046,China)

机构地区：[1]咸阳职业技术学院医药化工学院,陕西咸阳712000 [2]陕西省中药绿色制造技术协同创新中心,陕西国际商贸学院医药学院,陕西西安712046

出　　处：《化学工程师》2021年第10期11-14,共4页Chemical Engineer

基　　金：咸阳职业技术学院博士科研基金项目(No.2021BK01);咸阳职业技术学院科学研究基金资助项目(No.2020KJB02)。

摘　　要：本文报道6-氯-1,4-二氢-1,4-环氧萘(1)的合成与表征。以4-氯-2-碘苯酚(2)为原料,首先经过羟基保护得到4-氯-2-碘苯基-4-甲基苯磺酸酯(3),然后在异丙基溴化镁作用下原位生成苯炔中间体,再和呋喃发生Diels-Alder反应得到目标化合物(1),中间体及产物结构经核磁共振氢谱、碳谱和质谱表征。并重点讨论影响产物(1)收率的主要因素,确定最佳反应条件为:物料摩尔比n_(呋喃)∶n3=6∶1;异丙基溴化镁的最佳的用量为ni-PrMgBr∶n3=1.3∶1。在最佳合成条件下,6-氯-1,4-二氢-1,4-环氧萘(1)的收率达到66.5%。The synthesis and characterization of 6-chloro-1,4-dihydro-1,4-epoxynaphthalene(1)was reported.Using 4-chloro-2-iodophenol(2)as starting material,4-chloro-2-iodophenyl-4-methylbenzenesulfonate(3)was firstly obtained by hydroxyl protection,and then the benzyne intermediate was synthesized in situ by the reaction of i-PrMgBr,the target compound(1)was obtained by Diels-Alder reaction with Furan.The structure of the intermediate and the product were characterized by 1H NMR,13C NMR and MS.The main factors affecting the yield of product(1)were discussed.The optimum reaction conditions were determined as follows:the molar ratio of n_(furan)∶n3=6∶1;the dosage of i-PrMgBr was ni-PrMgBr∶n3=1.3∶1.Under the optimum conditions,the yield of 6-chloro-1,4-dihydro-1,4-epoxynaphthalene(1)was up to 66.5%.

关 键 词：萘衍生物 DIELS-ALDER反应 氧桥环化合物 苯炔 

分 类 号：TQ463[化学工程—制药化工]