3,4,5-trimethoxyphenol -Drug Synthesis Database

【结构式】

【分子编号】37163

【品名】3,4,5-trimethoxyphenol

【CA登记号】

【分子式】C₉H₁₂O₄

【分子量】184.19188

【元素组成】C 58.69% H 6.57% O 34.75%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(V)

By reaction of 3,4,5-trimethoxyphenoxyglycidylether (VI) [obtained by reaction of 3,4,5-trimethoxyphenol (V) with epichlorohydrine (II)] with 1-(2-methoxyphenyl)piperazine (I) in refluxing isopropanol.

参考文献中间体

合成目标

【1】 Kleemann, A.; DE 2814168 .
【2】 Engel, J.; Jakovlev, V.; Kleemann, A.; Enciprazine. Drugs Fut 1981, 6, 5, 278.

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)	11882	1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine	35386-24-4	C₁₁H₁₆N₂O	详情	详情
(II)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(V)	37163	3,4,5-trimethoxyphenol		C₉H₁₂O₄	详情	详情
(VI)	37164	2,3-dimethoxy-5-(2-oxiranylmethoxy)phenyl methyl ether; 2-[(3,4,5-trimethoxyphenoxy)methyl]oxirane		C₁₂H₁₆O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

Isovanillin (I) was protected as the allyl ether (III) by treatment with allyl bromide (II) and K2CO3. Aldehyde reduction of (III) with NaBH4 gave alcohol (IV), which was converted to chloride (V) using SOCl2. Condensation of chloride (V) with the sodium salt of 3,4,5-trimethoxyphenol (VI) produced the corresponding ether (VII). Finally, deprotection of the allyl group of (VII) was achieved by treatment with Wilkinson’s catalyst and DABCO.

参考文献中间体

合成目标

【1】 McGown, A.T.; Hadfield, J.A.; Rennison, D.; Woo, M.; Lawrence, N.J.; Antimitotic and cell growth inhibitory properties of combrestastatin A-4-like ethers. Bioorg Med Chem Lett 2001, 11, 1, 51.

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)	18455	3-hydroxy-4-methoxybenzaldehyde; Isovanillin	621-59-0	C₈H₈O₃	详情	详情
(II)	11463	3-Bromo-1-propene; 3-Bromopropene；allyl bromide	106-95-6	C₃H₅Br	详情	详情
(III)	48348	3-Allyloxy-4-methoxybenzaldehyde		C₁₁H₁₂O₃	详情	详情
(IV)	48349	[3-(allyloxy)-4-methoxyphenyl]methanol		C₁₁H₁₄O₃	详情	详情
(V)	48350	allyl 5-(chloromethyl)-2-methoxyphenyl ether; 2-(allyloxy)-4-(chloromethyl)-1-methoxybenzene		C₁₁H₁₃ClO₂	详情	详情
(VI)	37163	3,4,5-trimethoxyphenol		C₉H₁₂O₄	详情	详情
(VII)	48351	allyl 2-methoxy-5-[(3,4,5-trimethoxyphenoxy)methyl]phenyl ether; 5-[[3-(allyloxy)-4-methoxybenzyl]oxy]-1,2,3-trimethoxybenzene		C₂₀H₂₄O₆	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

The condensation of 3-aminno-4-phenylsulfonyl fluoride (II) with 3,4,5-trimethoxyphenol (I) in the presence of triethylamine furnished the sulfonate ester (III). The amino group of (III) was then acylated with N-Boc-beta-alanine (IV) using EDC and HOBt to yield amide (V). Finally, acid cleavage of the N-Boc protecting group of (V) provided the title aminopropionamide.

参考文献中间体

合成目标

【1】 Barr, K.J.; Gwaltney, S.L. II; Imade, H.M.; et al.; Novel sulfonate derivatives: Potent antimitotic agents. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 135.
【2】 Barr, K.J.; Steiner, B.A.; Qun, L.; Rosenberg, S.; Sham, H.; Gwaltney, S.L. II; Imade, H.M.; Woods, K.W. (Abbott Laboratories Inc.); Cell proliferation inhibitors. WO 0073264 .

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)	37163	3,4,5-trimethoxyphenol		C₉H₁₂O₄	详情	详情
(II)	51178	4-Methoxymetanilyl fluoride; 3-Amino-4-methoxybenzenesulfonyl fluoride	498-74-8	C₇H₈FNO₃S	详情	详情
(III)	51179	3,4,5-trimethoxyphenyl 3-amino-4-methoxybenzenesulfonate		C₁₆H₁₉NO₇S	详情	详情
(IV)	26616	N-(tert-butoxycarbonyl)-beta-alanine	3303-84-2	C₈H₁₅NO₄	详情	详情
(V)	51180	3,4,5-trimethoxyphenyl 3-([3-[(tert-butoxycarbonyl)amino]propanoyl]amino)-4-methoxybenzenesulfonate		C₂₄H₃₂N₂O₁₀S	详情	详情

Extended Information