新产品编号:574775
Chemical Name: 12-(4-Hydroxyphenyl)-1,12-dicarba-closo-dodecaborane(12)-1-methanol
CAS No. 227183-66-6
项目整合开发状态: Biological Testing
项目研究机构: University of Tokyo (Originator)
合成路线:1,12-Dicarba-closo-dodecaborane (I) was lithiated with n-butyllithium in 1,2-dimethoxyethane and subsequently converted to the C-copper(I) derivative (II) with cuprous chloride.Coupling of (II) with p-iodoanisole (III) in the presence of pyridine furnished the C-arylated compound (IV).This was converted to the C-methoxycarbonyl derivative (V) via formation of the corresponding lithiocarborane,and then treatment with methyl chloroformate.Reduction of the methyl ester group with LiAlH4 produced alcohol (VI).Finally,cleavage of the methyl ether by means of boron tribromide yielded the title compound.
📌 参考资料/链接：
参考文献标题:Potent estrogenic agonists bearing dicarba-closo-dodecaborane as a hydrophobic pharmacophore
文献作者:Endo,Y.; Iijima,T.; Yamakoshi,Y.; Yamaguchi,M.; Fukasawa,H.; Shudo,K.
参考来源:J Med Chem 1999,42(9),1501
📄 详细内容
合成路线:1,12-Dicarba-closo-dodecaborane (I) was lithiated with n-butyllithium in 1,2-dimethoxyethane and subsequently converted to the C-copper(I) derivative (II) with cuprous chloride.Coupling of (II) with p-iodoanisole (III) in the presence of pyridine furnished the C-arylated compound (IV).This was converted to the C-methoxycarbonyl derivative (V) via formation of the corresponding lithiocarborane,and then treatment with methyl chloroformate.Reduction of the methyl ester group with LiAlH4 produced alcohol (VI).Finally,cleavage of the methyl ether by means of boron tribromide yielded the title compound.
参考文献标题:Structure-activity of estrogenic agonists bearing dicarba-closo-dodecarbone.Effect of geometry and separation distance of hydroxyl groups at the ends of molecules
文献作者:Endo,Y.; Iijima,T.; Amakoshi,Y.; Kubo,A.; Itai,A.
参考来源:Bioorg Med Chem Lett 1999,9(23),3313