新型两亲性氮杂六芳基苯的合成  

Synthesis of A Novel Amphipathic Aza-hexaarylbenzene

作　　者：刘雨 曾旺 郭大政 金武松[1] 李贤英[2] 张灯青[1] LIU Yu;ZENG Wang;GUO Da-zheng;JIN Wu-song;LI Xian-ying;ZHANG Deng-qing(College of Chemistry,Chemical Engineering and Biotechnology,Donghua University,Shanghai 201620,China;College of Environmental Science and Engineering,Donghua University,Shanghai 201620,China)

机构地区：[1]东华大学化学化工与生物工程学院,上海201620 [2]东华大学环境科学与工程学院,上海201620

出　　处：《合成化学》2020年第1期41-45,共5页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21672036,21302018)

摘　　要：以5-溴-2-十二烷基嘧啶为原料,经Sonogashira偶联等反应制得1,2-双(2-十二烷基嘧啶-5-基)乙炔(4);1-溴-4-(2-(2-(2-甲氧基乙氧基)乙氧基)乙氧基)苯(5)与双频哪醇合二硼反应制得化合物(6);4,4′-二溴苯偶酰与1,3-二苯基丙酮经羟醛缩合反应制得四芳基环戊二烯酮衍生物(7);化合物4与7经Diels-Alder反应制得化合物8;8与6通过Suzuki-Miyaura偶联反应合成新型两亲性氮杂六芳基苯(9),化合物6~9为新化合物,其结构经1 H NMR,13 C NMR和HR-MS(MALDI-TOF)表征。1,2-Bis(2-dodecylpyrimidin-5-yl)ethyne(4)was synthesized by Sonogashira coupling reaction.1-Bromo-4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene(5)was treated with bis(pinacolato)diboron to give compound 6 through Suzuki coupling reaction.Compound 7 was prepared by Aldol reaction of 4,4′-dibromobenzyl with 1,3-diphenylacetone.Then compound 4 and 7 to afford compound 8 by Diels-Alder reaction.Compound 8 was further reacted with compound 6 to give target product 9 by Suzuki-Miyaura coupling reaction.6~9 were novel compounds.The structures were characterized by 1 H NMR,13 C NMR and HR-MS(MALDI-TOF).

关 键 词：5-溴-2-十二烷基嘧啶 SONOGASHIRA偶联反应 Suzuki-Miyaura偶联反应 DIELS-ALDER反应 合成 

分 类 号：O625.6[理学—有机化学] O626[理学—化学]