2-{[4-(decyloxy)phenoxy]methyl}oxirane; decyl 4-(2-oxiranylmethoxy)phenyl ether -Drug Synthesis Database

【结构式】

【分子编号】58572

【品名】2-{[4-(decyloxy)phenoxy]methyl}oxirane; decyl 4-(2-oxiranylmethoxy)phenyl ether

【CA登记号】

【分子式】C₁₉H₃₀O₃

【分子量】306.4454

【元素组成】C 74.47% H 9.87% O 15.66%

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：(V)

Monoalkylation of hydroquinone (I) with decyl bromide (II) under basic conditions provided 4-(decyloxy)phenol (III), which was further condensed with epichlorohydrin (IV) in the presence of Cs2CO3 to yield the glycidyl ether (V). Ring opening of epoxide (V) with allyl 4-hydroxybenzoate (VI) furnished adduct (VII). Then, oxidation of the secondary alcohol (VII) using the Dess-Martin reagent afforded the keto ester (VIII), which upon deprotection with palladium tetrakis(triphenylphosphine) gave the target carboxylic acid.

参考文献中间体

合成目标

【1】 Connolly, S.; Botterll, S.; Bennion, C.; et al.; Design and synthesis of a novel and potent series of inhibitors of cytosolic phospholipase A2 based on a 1,3-disubstituted propan-2-one skeleton. J Med Chem 2002, 45, 6, 1348.

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)	13163	p-Dihydrobenzene; Hydroquinone	123-31-9	C₆H₆O₂	详情	详情
(II)	58570	1-Bromodecane; 1-Decyl bromide; Decyl bromide; n-decyl bromide	112-29-8	C₁₀H₂₁Br	详情	详情
(III)	58571	4-Decyloxyphenol		C₁₆H₂₆O₂	详情	详情
(IV)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(V)	58572	2-{[4-(decyloxy)phenoxy]methyl}oxirane; decyl 4-(2-oxiranylmethoxy)phenyl ether		C₁₉H₃₀O₃	详情	详情
(VI)	21022	allyl 4-hydroxybenzoate		C₁₀H₁₀O₃	详情	详情
(VII)	58573	allyl 4-{3-[4-(decyloxy)phenoxy]-2-hydroxypropoxy}benzoate		C₂₉H₄₀O₆	详情	详情
(VIII)	58574	allyl 4-{3-[4-(decyloxy)phenoxy]-2-oxopropoxy}benzoate		C₂₉H₃₈O₆	详情	详情

Extended Information