2,6-di(tert-butyl)-4-methylene-2,5-cyclohexadien-1-one -Drug Synthesis Database

【结构式】

【分子编号】59791

【品名】2,6-di(tert-butyl)-4-methylene-2,5-cyclohexadien-1-one

【CA登记号】

【分子式】C₁₅H₂₂O

【分子量】218.33908

【元素组成】C 82.52% H 10.16% O 7.33%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XI)

An improved synthesis has been reported. Acid-catalyzed ketalization of aldehyde (VIII) with trimethyl orthoformate provided the dimethyl acetal (IX) which, upon thermal decomposition in refluxing xylene, gave rise to the alpha-methoxy methylenequinone derivative (X). This was then condensed with the lithio derivative of sultam (III) to form selectively the desired E-adduct. In an analogous procedure, aldehyde (VIII) was converted to the chloromethylene compound (XI) with methanesulfonyl chloride and triethylamine in refluxing CH2Cl2. Condensation of (XI) with the lithiated sultam (III) furnished the desired E-benzylidene sultam.

参考文献中间体

合成目标

【1】 Inagaki, M.; Haga, N.; Kobayashi, M.; Ohta, N.; Kamata, S.; Tsuri, T.; Highly E-selective and effective synthesis of antiarthritic drug candidate S-2474 using quinone methide derivatives. J Org Chem 2002, 67, 1, 125.
【2】 Haga, N.; Inagaki, M.; Matsumoto, S.; Kamata, S. (Shionogi & Co. Ltd.); Method for producing benzylidene derivs.. EP 0626377 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	59785	2-ethyl-1lambda~6~-isothiazolidine-1,1-dione		C₅H₁₁NO₂S	详情	详情
(VIII)	14875	3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzaldehyde; 3,5-di(tert-butyl)-4-hydroxybenzaldehyde; 3,5-Di-tert-butyl-4-hydroxybenzaldehyde	1620-98-0	C₁₅H₂₂O₂	详情	详情
(IX)	59789	2,6-di(tert-butyl)-4-(dimethoxymethyl)phenol		C₁₇H₂₈O₃	详情	详情
(X)	59790	2,6-di(tert-butyl)-4-(methoxymethylene)-2,5-cyclohexadien-1-one		C₁₆H₂₄O₂	详情	详情
(XI)	59791	2,6-di(tert-butyl)-4-methylene-2,5-cyclohexadien-1-one		C₁₅H₂₂O	详情	详情

Extended Information