allyl 4-hydroxybenzoate -Drug Synthesis Database

【结构式】

【分子编号】21022

【品名】allyl 4-hydroxybenzoate

【CA登记号】

【分子式】C₁₀H₁₀O₃

【分子量】178.1876

【元素组成】C 67.41% H 5.66% O 26.94%

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：(III)

Adamantylbenzoic acid (I) was converted to acid chloride (II) on treatment with SOCl2, and subsequently condensed with allyl p-hydroxybenzoate (III) in the presence of Et3N to afford the benzoyloxybenzoic ester (IV). The allyl ester was then cleaved by refluxing in aqueous ethanol in the presence of tris(triphenylphosphine)rhodium chloride to yield the title compound.

参考文献中间体

合成目标

【1】 Shroot, B.; Eustache, J.; Bernardon, J.-M. (CIRD Galderma); Aromatic esters and thioesters, process for their preparation and their use in human or animal therapeutics and in cosmetics. AU 8928608; EP 0325540 .
【2】 Eustache, J.; Bernardon, J.-M.; Shroot, B. (CIRD Galderma); Aromatic esters and thioesters, a process for their preparation and their use in human or veterinary medicine and in cosmetic compsns.. US 5173289 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	21020	3-(1-adamantyl)-4-methoxybenzoic acid	C₁₈H₂₂O₃	详情	详情
(II)	21021	3-(1-adamantyl)-4-methoxybenzoyl chloride	C₁₈H₂₁ClO₂	详情	详情
(III)	21022	allyl 4-hydroxybenzoate	C₁₀H₁₀O₃	详情	详情
(IV)	21023	4-[(allyloxy)carbonyl]phenyl 3-(1-adamantyl)-4-methoxybenzoate	C₂₈H₃₀O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

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