BR-630
Chemical Name: 4-[2,3,4,5,6,7,8,9,10,11-Decamethyl-1,12-dicarba-closo-dodecaboran(12)-1-ylcarboxamido]benzoic acid
CAS No. 296782-99-5
项目整合开发状态: Biological Testing
项目研究机构: University of Tokyo (Originator)
合成路线:Methylation of 1,12-dicarba-closo-dodecaborane (I) with methyl triflate at 130 C in a sealed vessel afforded the decamethyl borane (II).Lithiation of (II) with methyllithium and subsequent quenching with CO2 produced the carboxylic acid (III),which was further converted to the corresponding acid chloride (IV) by treatment with SOCl2.Condensation of acid chloride (IV) with ethyl 4-aminobenzoate (V) in o-dichlorobenzene at 180 C gave amide (VI).Finally,basic hydrolysis of the ethyl ester group of (VI) furnished the title carboxylic acid.
📌 参考资料/链接：
参考文献标题:Polymethylcarborane as a novel biactive moiety: Derivatives with potent retinoid antagonistic activity
文献作者:Endo,Y.; Yaguchi,K.; Kawachi,E.; Kagechika,H.
参考来源:Bioorg Med Chem Lett 2000,10(15),1733
📄 详细内容
合成路线:Methylation of 1,12-dicarba-closo-dodecaborane (I) with methyl triflate at 130 C in a sealed vessel afforded the decamethyl borane (II).Lithiation of (II) with methyllithium and subsequent quenching with CO2 produced the carboxylic acid (III),which was further converted to the corresponding acid chloride (IV) by treatment with SOCl2.Condensation of acid chloride (IV) with ethyl 4-aminobenzoate (V) in o-dichlorobenzene at 180 C gave amide (VI).Finally,basic hydrolysis of the ethyl ester group of (VI) furnished the title carboxylic acid.
参考文献标题:Functionalization of polymethylcarboranes.Preparation and reactivity of 2,3,4,5,6,7,8,9,10,11-decamethyl-1,12-dicarba-closo-dodecaborane(12)-1-carboxylic acid
文献作者:Endo,Y.; et al.
参考来源:Chem Pharm Bull 1999,47(5),699