1-Bromodecane; 1-Decyl bromide; Decyl bromide; n-decyl bromide -Drug Synthesis Database

【结构式】

【分子编号】58570

【品名】1-Bromodecane; 1-Decyl bromide; Decyl bromide; n-decyl bromide

【CA登记号】112-29-8

【分子式】C₁₀H₂₁Br

【分子量】221.18074

【元素组成】C 54.3% H 9.57% Br 36.13%

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：(II)

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

合成路线2

该中间体在本合成路线中的序号：(II)

Alkylation of diethyl acetamidomalonate (I) with 1-bromodecane (II) affords malonate (III). Subsequent hydrolysis and decarboxylation of (III) under acidic conditions leads to 2-aminododecanoic acid (IV). This is then protected as the N-Boc derivative (V) upon treatment with Boc2O and NaOH

参考文献中间体

合成目标

【1】 Blanchfield, J.T.; Dutton, J.L.; Hogg, R.C.; Gallagher, O.P.; Craik, D.J.; Jones, A.; Adams, D.J.; Lewis, R.J..; Alewood, P.F.; Toth, I.; Synthesis, structure elucidation, in vitro biological activity, toxicity, and caco-2 cell permeability of lipophilic analogues of alpha-conotoxin MII. J Med Chem 2003, 46, 7, 1266.

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)	16710	Diethyl 2-(acetamido)malonate; Diethyl acetamidomalonate	1068-90-2	C₉H₁₅NO₅	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)	63516	diethyl 2-(acetylamino)-2-decylpropanedioate		C₁₉H₃₅NO₅	详情	详情
(IV)	63517	2-aminododecanoic acid		C₁₂H₂₅NO₂	详情	详情
(V)	63518	2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)dodecanoic acid		C₁₇H₃₃NO₄	详情	详情

Extended Information