邻羟基芳香N-叔丁基亚磺酰亚胺的微波合成研究  

Study on Synthesis of ortho-Hydroxyl Aromatic N-tert-Butylsulfinyl Imines under Microwave Irradiation

作　　者：赵云辉[1,2] 任新芳 刘汉文[1,2] 唐子龙[1,2] 

机构地区：[1]湖南科技大学化学化工学院,湘潭411201 [2]理论化学与分子模拟省部共建教育部重点实验室,湘潭411201

出　　处：《有机化学》2014年第6期1218-1221,共4页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21372070);湖南省科学基金课题(No.11JJ3016);湖南省教育厅基金(No.B31314)资助项目~~

摘　　要：手性N-叔丁基亚磺酰亚胺是一类非常重要的有机化学合成中间体.报道以水杨醛类化合物1和N-叔丁基亚磺酰胺(2)为原料,分别以硫酸氢钾、碳酸铯为促进剂在微波辐射条件下反应,合成得到11种未见文献报道的水杨醛类N-叔丁基亚磺酰亚胺(3),产率中等到良好.研究发现:带有强吸电子基的底物在硫酸氢钾的作用下,产率较高;而带有强供电子基化合物、取代基位阻大的化合物在碳酸铯的作用下反应效果较好.所有新化合物均通过红外光谱、核磁共振谱、高分辨质谱对其结构进行了确认.Chiral N-tert-butanesulfinyl imines have been shown to be important intermediates for asymmetric synthesis in recent years. Eleven new（R,E）-N-（2-hydroxybenzylidene）-tert-butyl-sulfinamides（3） were synthesized from salicylaldehydes 1 and chiral tert-butanesulfinamide 2 under microwave irradiation in moderate to good yields. The reaction could work well in the mixture of KHSO4/PhMe or Cs2CO3/CH2Cl2. And the results show that the KHSO4/PhMe reaction system is helpful for the salicylaldehydes with electron-donating group; however, the Cs2CO3/CH2Cl2 reaction system is applicable to the salicylaldehydes with electron-deficient group and steric hindrance group. The structures of these new compounds were determined by 1H NMR, 13C NMR, IR and HRMS.

关 键 词：微波 手性亚胺 N-叔丁基亚磺酰胺 水杨醛 

分 类 号：O621.3[理学—有机化学]