1-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-propen-1-ol -Drug Synthesis Database

【结构式】

【分子编号】30022

【品名】1-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-propen-1-ol

【CA登记号】

【分子式】C₁₅H₂₀O₃

【分子量】248.322

【元素组成】C 72.55% H 8.12% O 19.33%

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)

In a related method for obtaining the precursor (V), epoxide (II) was condensed with the tosyl-protected tetraamine (XIII) in an autoclave at 170 C to give (XIV). The N-tosyl groups of (XIV) were then removed by treatment with lithium metal in liquid ammonia, yielding intermediate (III), which was then subjected to alkylation with bromoacetic acid, followed by acid hydrolysis

参考文献中间体

合成目标

【1】 Platzek, J.; Gries, H.; Weinmann, H.-J.; Schuhmann-Giampieri, G.; Press, W.-R. (Schering AG); 1,4,7,10-Tetraazacyclododecane-butyl-triols, process for their preparation, and pharmaceutical agents containing these cpds.. DE 4009119; EP 0448191; US 2002176823; US 6399043 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	23660	2-Bromoacetic acid	79-08-3	C₂H₃BrO₂	详情	详情
(II)	30022	1-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-propen-1-ol		C₁₅H₂₀O₃	详情	详情
(III)	60023	(5S,6R)-2,2-dimethyl-6-(1,4,7,10-tetraazacyclododecan-1-yl)-1,3-dioxepan-5-ol		C₁₅H₃₂N₄O₃	详情	详情
(V)	60025	2-[4-[(1R,2S)-2,3-dihydroxy-1-(hydroxymethyl)propyl]-7,10-bis(2-hydroxy-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl]acetic acid		C₁₈H₃₄N₄O₉	详情	详情
(XIII)	60032	1,4,7-tris[(4-methylphenyl)sulfonyl]-1,4,7,10-tetraazacyclododecane		C₂₉H₃₈N₄O₆S₃	详情	详情
(XIV)	60033	(5S,6R)-2,2-dimethyl-6-{4,7,10-tris[(4-methylphenyl)sulfonyl]-1,4,7,10-tetraazacyclododecan-1-yl}-1,3-dioxepan-5-ol		C₃₆H₅₀N₄O₉S₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The Grignard reaction of 3-(cyclopentyloxy)-4-methoxybenzaldehyde (I) with vinylmagnesium bromide in THF gives the vinyl carbinol (II), which is oxidized with MnO2 in ethyl acetate yielding the propenone (III). The condensation of (III) with pyridine-2-carbaldehyde (IV) by means of 3-ethyl-5-(2-hydroxyethyl)-4-methyl-thiazolium bromide (ETB) and triethylamine affords the butanedione (V), which is finally cyclized to the target compound with p-toluenesulfonic acid in refluxing toluene.

参考文献中间体

合成目标

【1】 Rasori, R.; Robichaud, A.; Girard, Y.; MacDonal, D.; Laliberté, F.; Huang, z.; Perrier, H.; Bayly, C.; Substituted furans as inhibitors of the PDE4 enzyme. Bioorg Med Chem Lett 1999, 9, 3, 323.
【2】 Young, R.N.; MacDonald, D.; Bayly, C.; Perrier, H.; Han, Y.; Giroux, A. (Merck Frosst Canada Inc.); Aryl furan derivs. as PDE IV inhibitors. EP 1021429; US 6020339; WO 9918095 .

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)	16510	3-(cyclopentyloxy)-4-methoxybenzaldehyde		C₁₃H₁₆O₃	详情	详情
(II)	30022	1-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-propen-1-ol		C₁₅H₂₀O₃	详情	详情
(III)	30023	1-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-propen-1-one		C₁₅H₁₈O₃	详情	详情
(IV)	25173	2-pyridinecarbaldehyde	1121-60-4	C₆H₅NO	详情	详情
(V)	30024	1-[3-(cyclopentyloxy)-4-methoxyphenyl]-4-(2-pyridinyl)-1,4-butanedione		C₂₁H₂₃NO₄	详情	详情

Extended Information