5-烷氧基-4-环胺基-3-卤-2(5H)-呋喃酮的合成与表征有机化学.pdfVIP

2011 年第 31 卷 有 机 化 学 Vol. 31, 2011 第 9 期, 1460～1467 Chinese Journal of Organic Chemistry No. 9, 1460～1467 ·研究论文· 5-烷氧基-4-环胺基-3- 卤-2(5H)-呋喃酮的合成与表征 傅建花 a 汪朝阳*,a 郝志峰 b 霍景沛 a (a 华南师范大学化学与环境学院 广州 510006) (b 广东工业大学轻工化工学院 广州 510006) 摘要 在氟化钾作用下, 亲核试剂环状仲胺与 5-烷氧基-3,4-二卤-2(5H)-呋喃酮在室温下发生串联的迈克尔加成-消除 反应, 合成了 17 个新化合物. 通过旋光度, UV-Vis, IR, 1H NMR, 13C NMR, MS, 元素分析和 X 射线单晶衍射等表征方 法, 确定了目标化合物的化学结构和绝对构型. 关键词 5-烷氧基-3,4-二卤-2(5H)-呋喃酮; 环状仲胺; 迈克尔加成; 串联反应; 5-烷氧基-4-环胺基-3- 卤-2(5H)-呋喃酮; 合成 Syntheses and Characterization of 5-Alkoxy-4-cycloamino-3- halo-5H-furan-2-one Fu, Jianhuaa Wang, Zhaoyang*,a Hao, Zhifengb Huo, Jingpeia a ( School of Chemistry and Environment, South China Normal University, Guangzhou 510006) (b Faculty of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006) Abstract Using cyclic secondary amines as nucleophilic reagents, the tandem Michael addi- tion-elimination of 5-alkoxy-3,4-dihalo-5H-furan-2-one in the presence of potassium fluoride gave 17 novel compounds. The chemical structures and absolute configurations of the new compounds were confirmed via 1 13 rotation, UV-Vis, IR, H NMR, C NMR, MS, elemental analysis and X-ray single crystal diffraction. Keywords 5-alkoxy-3,4-dihalo-5H-furan-2-one; cyclic secondary amine; Michael addition; tandem reac- tion; 5-alkoxy-4-cycloamino-3-halo-5H-furan-2-one; synthesis 许多天然产物含有 2(5H)-呋喃酮的结构单元, 而且