新型2-苯并噻吩酮亚胺的合成与应用  

Synthesis and Application of Novel 2-Benzothiophenone-derived-ketimines

作　　者：付晓慧 刘海辉 彭巧巧 陆纪宏 游勇 周鸣强[1,3] 赵建强 葛真真[1,3] 袁伟成 FU Xiaohui;LIU Haihui;PENG Qiaoqiao;LU Jihong;YOU Yong;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,China;Institute for Advanced Study,Chengdu University,Chengdu 610106,China;University of Chinese Academy of Sciences,Beijing 100049,China;Zhejiang Jinhua Conba Bio-Pharm.Co.,Ltd.,Jinhua 100038,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 [4]浙江金华康恩贝生物制药有限公司,浙江金华100038

出　　处：《合成化学》2025年第3期140-144,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);四川省科技厅项目(2024NSFSC0281)。

摘　　要：酮亚胺具有良好的反应活性,在合成含氮的天然产物和药物分子中具有重要的作用,因此开发一种高效且简便的2-苯并噻吩N-Boc酮亚胺的合成策略是十分必要的。本文用苯并噻吩二酮为原料,通过经典的维蒂希反应,以21%~68%的收率首次合成了新型的2-苯并噻吩N-Boc酮亚胺产物(3a~3i),并拓展了9个不同取代基的底物。尝试了其在消旋磷酸催化下与吲哚的傅-克烷基化反应,成功构建了含有一个季碳中心的(2-(1H-吲哚-3-基)-5-甲基-3-氧代-2,3-二氢苯并噻吩-2-基)氨基甲酸叔丁酯(5),收率高达99%,并对这些化合物的结构进行了^(1)H NMR、^(13)C NMR和HR-MS(ESI-TOF)表征。Ketimines have good reactivity and play an important role in the synthesis of nitrogencontaining natural products and drug molecules.Therefore,it is necessary to develop an efficient and simple strategy for the synthesis of 2-benzothiophene ketone imines.In this paper,nine novel tert-butyl(Z)-(3-oxobenzo[b]thiophen-2(3H)-ylidene)carbamates of benzothiophene ketones(3a~3i)were obtained in one step with a yield of 21%~68%using benzothiophene ketones as raw material through the classical Wittig reaction.The friedel-crafts alkylation reaction of the benzothiophene ketone with indole under the catalysis of racemic phosphoric acid was investigated,and the product containing a quaternary carbon center(5)was successfully constructed,yield of 99%.These products were characterized by^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).

关 键 词：苯并噻吩酮亚胺 吲哚 维蒂希反应 合成 消旋磷酸 

分 类 号：O621.3[理学—有机化学]