3-[6-(1,2-diboriran-3-yl)hexaboranyl]-1,2-diborirane -Drug Synthesis Database

【结构式】

【分子编号】42007

【品名】3-[6-(1,2-diboriran-3-yl)hexaboranyl]-1,2-diborirane

【CA登记号】

【分子式】C₂H₁₂B₁₀

【分子量】144.22728

【元素组成】C 16.66% H 8.39% B 74.96%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

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.

参考文献中间体

合成目标

【1】 Fukasawa, H.; Endo, Y.; Shudo, K.; Yamakoshi, Y.; Yamaguchi, M.; Iijima, T.; Potent estrogenic agonists bearing dicarba-closo-dodecaborane as a hydrophobic pharmacophore. J Med Chem 1999, 42, 9, 1501.
【2】 Endo, Y.; et al.; Structure-activity of estrogenic agonists bearing dicarba-closo-dodecarbone. Effect of geometry and separation distance of hydroxyl groups at the ends of molecules. Bioorg Med Chem Lett 1999, 9, 23, 3313.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	42007	3-[6-(1,2-diboriran-3-yl)hexaboranyl]-1,2-diborirane		C₂H₁₂B₁₀	详情	详情
(II)	42008	[3-[6-(1,2-diboriran-3-yl)hexaboranyl]-1,2-diboriran-3-yl]copper		C₂H₁₁B₁₀Cu	详情	详情
(III)	31009	1-iodo-4-methoxybenzene; 4-iodophenyl methyl ether	696-62-8	C₇H₇IO	详情	详情
(IV)	42009	3-[6-(1,2-diboriran-3-yl)hexaboranyl]-3-(4-methoxyphenyl)-1,2-diborirane; 4-[3-[6-(1,2-diboriran-3-yl)hexaboranyl]-1,2-diboriran-3-yl]phenyl methyl ether		C₉H₁₈B₁₀O	详情	详情
(V)	42010	methyl 3-[6-[3-(4-methoxyphenyl)-1,2-diboriran-3-yl]hexaboranyl]-1,2-diborirane-3-carboxylate		C₁₁H₂₀B₁₀O₃	详情	详情
(VI)	42011	(3-[6-[3-(4-methoxyphenyl)-1,2-diboriran-3-yl]hexaboranyl]-1,2-diboriran-3-yl)methanol		C₁₀H₂₀B₁₀O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

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.

参考文献中间体

合成目标

【1】 Endo, Y.; et al.; 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. Chem Pharm Bull 1999, 47, 5, 699.
【2】 Kagechika, H.; Yaguchi, K.; Kawachi, E.; Endo, Y.; Polymethylcarborane as a novel biactive moiety: Derivatives with potent retinoid antagonistic activity. Bioorg Med Chem Lett 2000, 10, 15, 1733.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	42007	3-[6-(1,2-diboriran-3-yl)hexaboranyl]-1,2-diborirane		C₂H₁₂B₁₀	详情	详情
(II)	46964	3-[6-(1,2-dimethyl-1,2-diboriran-3-yl)-1,2,3,4,5,6-hexamethylhexaboranyl]-1,2-dimethyl-1,2-diborirane		C₁₂H₃₂B₁₀	详情	详情
(III)	46965	3-[6-(1,2-dimethyl-1,2-diboriran-3-yl)-1,2,3,4,5,6-hexamethylhexaboranyl]-1,2-dimethyl-1,2-diborirane-3-carboxylic acid		C₁₃H₃₂B₁₀O₂	详情	详情
(IV)	46966	3-[6-(1,2-dimethyl-1,2-diboriran-3-yl)-1,2,3,4,5,6-hexamethylhexaboranyl]-1,2-dimethyl-1,2-diborirane-3-carbonyl chloride		C₁₃H₃₁B₁₀ClO	详情	详情
(V)	16498	Benzocaine; ethyl 4-aminobenzoate	94-09-7	C₉H₁₁NO₂	详情	详情
(VI)	46967	ethyl 4-[([3-[6-(1,2-dimethyl-1,2-diboriran-3-yl)-1,2,3,4,5,6-hexamethylhexaboranyl]-1,2-dimethyl-1,2-diboriran-3-yl]carbonyl)amino]benzoate		C₂₂H₄₁B₁₀NO₃	详情	详情

Extended Information