二芳基(联茚满)二酮类化合物的合成  

Synthesis of Diaryl Biindenylidenedione Compound

作　　者：杜笑 唐羽琴 陈炜俞 马爱军 DU Xiao;TANG Yuqin;CHEN Weiyu;MA Aijun(School of Biotecology and Health Sciences,Wuyi University,Jiangmen 529020,China)

机构地区：[1]五邑大学生物科技与大健康学院,广东江门529020

出　　处：《合成化学》2024年第8期737-742,共6页Chinese Journal of Synthetic Chemistry

基　　金：广东省乡村振兴战略专项资金(“大专项+任务清单”)资助项目(江科[2021]183);广东省教育厅“创新强校”工程重点领域专项项目(2023ZDZX2068);五邑大学港澳联合研发基金资助项目(2021WGALH12)。

摘　　要：联茚满二酮类化合物不仅是众多天然产物和活性药物分子的核心骨架,也是许多新型光致变色材料的结构单元。以邻苯二甲醇为原料,经过硅基保护反应、偶联反应、脱除保护基反应、Dess-Martin氧化反应、Pinnick氧化反应、羧酸重氮化以及重氮酮环化合成二芳基(联茚满)二酮类化合物(8),总收率18%。化合物3~8的结构经^(1)H NMR、^(13)C NMR、HR-MS(ESI)和X-Ray表征。此外,还对化合物4和化合物8合成过程中的机理进行分析。该合成方法具有起始原料简单易得,路线新颖且高效的优点。Diaryl biindenylidenedione compounds are not only the core backbone of numerous natural products and active drug molecules,but also the structural units of many new photochromic materials.Diaryl(biindene)diketone compound 8 was synthesized from ortho benzyl alcohol through silicon based protection reaction,coupling reaction,deprotection reaction,Dess-Martin oxidation,Pinnick oxidation,carboxylic acid diazotization,and diazone cyclization,total yield 18%.The structures of compounds 3~8 were confirmed by ^(1)H NMR,^(13)C NMR,HR-MS(ESI),and X-Ray.This article also analyzes the mechanism of the synthesis process of compound 4 and compound 8.This synthesis method has the advantages of simple and easily available starting materials,novel routes,and high efficiency.

关 键 词：重氮酮环化反应 Dess-Martin氧化反应 Pinnick氧化反应 联茚满二酮类化合物 光致变色材料 合成 

分 类 号：O62[理学—有机化学]