2-乙炔基-2-苯基环丁烷的合成  

Synthesis of 2-Ethynyl-2-phenyloxetane

作　　者：陈炎 周鸣强[1,3] 赵建强 葛真真[1,3] 袁伟成 CHEN Yan;ZHOU Mingqiang;ZHAO Jianqiang;GE Zhenzhen;YUAN Weicheng(National Engineering Research Center of Chiral Drugs,Chengdu Institute of Organic Chemistry,Chinese Academy of Sciences,Chengdu 610041;Institute for Advanced Study,Chengdu University,Chengdu 610106,China;University of Chinese Academy of Sciences,Beijing 100049,China)

机构地区：[1]中国科学院成都有机化学研究所,手性药物国家工程研究中心,四川成都610041 [2]成都大学高等研究院,四川成都610106 [3]中国科学院大学,北京100049

出　　处：《合成化学》2025年第2期81-85,共5页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(22302021,22271027,22171029)。

摘　　要：构建无环结构的四取代叔碳是合成化学中最具挑战性的任务之一。以3-氯代苯丙酮为起始原料,以37%~50%的总收率合成了8个新型的2-乙炔基-2-苯基环丁烷衍生物(3a~3h),其作为具有较大环张力的小杂环化合物,极易发生开环反应和扩环反应。同时,初步尝试了铜催化的苯胺与2-乙炔基-2-苯基氧杂环丁烷的炔丙基化反应,得到了四取代γ-氨基醇(5)。最后对这些化合物的结构进行了^(1)H NMR和^(13)C NMR表征。The construction of acyclic-tetrasubstituted tertiary carbons remains one of the most challenging tasks in synthetic chemistry.In this manuscript,we obtained eight structurally novel 2-ethynyl-2-phenyloxetane derivatives(3a~3h)using 3-chloro-1-phenylpropan-1-one as starting material with a total yield of 37%to 50%.As small heterocycles compounds with a large ring tension,they are prone to ring opening and ring expanding reactions.Meanwhile,we initially attempted Cu-catalyzed propargylization reaction between aniline and 2-acetylidene-2-phenyloxy-heterocyclobutane and the tetrasubstitutedγ-amino alcohol(5)was obtained.These compounds were characterized by ^(1)H NMR and ^(13)C NMR.

关 键 词：3-氯代苯丙酮 2-乙炔基-2-苯基氧杂环丁烷 炔丙基化 开环 合成 铜催化 四取代γ-氨基醇 

分 类 号：O621.3[理学—有机化学]