一锅法合成2-羟基-9-芴酮类化合物  

One-pot Synthesis of 2-Hydroxy-9 H-fluoren-9-one Compounds

作　　者：朱启萌 姜雅坤 武超芊 毛亚兰 范晓语 王程宇 ZHU Qimeng;JIANG Yakun;WU Chaoqian;MAO Yalan;FAN Xiaoyu;WANG Chengyu(School of Chemistry and Chemical Engineering,Linyi University,Linyi 276000,China)

机构地区：[1]临沂大学化学化工学院,山东临沂276000

出　　处：《合成化学》2022年第10期790-796,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21702088);大学生创新创业项目(X202110452033)。

摘　　要：芴酮骨架的构建对于相关天然产物合成、药物分子结构修饰以及光电材料开发等具有重要意义。以苯环作为桥连基团,将呋喃环及炔酮片段构建在同一个分子内,设计并合成了邻呋喃芳基炔酮底物(1a)。利用化合物1a分子内呋喃环与炔键的D-A反应,在酸性条件下环氧开环,进而芳构化,一锅法合成了2-羟基-9-芴酮衍生物2a~2e,收率89%~96%,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI)表征。其中,化合物2a结构由X-ray单晶衍射确定。2a(CCDC:2144829)属单斜晶系,空间群P 21/c,晶胞参数a=3.9458(10),b=22.4460(7),c=14.7092(5),V=1294.1300(7)3,Dc=1.3980 Mg/m^(3),Z=4,F(000)=568。The fluorenones are of great importance in natural products,pharmaceuticals and optoelectronic materials.The 1-(o-furyl)aryl-ynone substrate(1a)proceeds through the cascade intramolecular Diels-Alder cycloaddition of furan and alkyne(IMDAF),acidic ring-opening of epoxide intermediate and re-aromatization sequence,affording the 2-hydroxy-9-fluorenone derivatives 2a~2e in 89%~96%yields.The structure of 2-hydroxy-9-fluorenone was confirmed by ^(1)H NMR,^(13)C NMR and HR-MS(ESI).Particularly,the structure of 2a was ambiguously confirmed by X-ray single crystal diffraction.The compound 2a(CCDC:2144829)belong to monoclinic with space group of P 21/c,unit cell dimensions of a=3.94580(10),b=22.4460(7),c=14.7092(5),V=1294.13(7)3,and Dc=1.398 Mg/m^(3),Z=4,F(000)=568.

关 键 词：芴酮 D-A反应 环氧开环 芳构化 一锅法 合成 

分 类 号：O621.3[理学—有机化学]