5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one -Drug Synthesis Database

【结构式】

【分子编号】30012

【品名】5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

【CA登记号】520-34-3

【分子式】C₁₆H₁₂O₆

【分子量】300.26768

【元素组成】C 64% H 4.03% O 31.97%

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：(I)

The alkylation of diosmetin (I) with allyl bromide in the presence of NaH in DMF furnished the triallyl ether (II). Claisen rearrangement of (II) in refluxing trichlorobenzene then gave the title compound.

参考文献中间体

合成目标

【1】 Wierzbicki, M.; Boussard, M.-F.; Verbeuren, T.; Vallez, M.-O.; Canet, E.; Rolland, Y. (ADIR et Cie.); Diosmetin derivs., process for their preparation and pharmaceutical compsns. containing them. CA 2161297; EP 0709383; FR 2726273; JP 1996225563; US 5629339 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	11463	3-Bromo-1-propene; 3-Bromopropene；allyl bromide	106-95-6	C₃H₅Br	详情	详情
(I)	30012	5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one	520-34-3	C₁₆H₁₂O₆	详情	详情
(II)	32941	5,7-bis(allyloxy)-2-[3-(allyloxy)-4-methoxyphenyl]-4H-chromen-4-one		C₂₅H₂₄O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

The reductocondensation of 2,3,4-trimethoxybenzaldehyde (I) with ethyl piperazine-1-carboxylate (II) by means of NaBH3CN in AcOH gives the corresponding benzyl derivative (III), which is decarboxylated with aqueous KOH at 130 C yielding 1-(2,3,4-trimethoxybenzyl)piperazine (IV). The acylation of (IV) with chloroacetyl chloride in dichloromethane affords 1-(2-chloroacetyl)-4-(2,3,4-trimethoxybenzyl)piperazine (V)., which is finally condensed with diosmetin (VI) by means of KHCO3 in DMF.

参考文献中间体

合成目标

【1】 Ferté, J.; Kühnel, J.-M.; Chapuis, G.; Rolland, Y.; Lewin, G.; Schwaller, M.A.; Flavonoid-related modulators of multidrug resistance: Synthesis, pharmacological activity, and structure-activity relationships. J Med Chem 1999, 42, 3, 478.

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)	22119	2,3,4-trimethoxybenzaldehyde	2103-57-3	C₁₀H₁₂O₄	详情	详情
(II)	24694	N-ethoxycarbonylpiperidine; Ethyl 1-piperazinecarboxylate; N-Ethoxycarbonyl piperazine; N-Carbethoxy piperazine	120-43-4	C₇H₁₄N₂O₂	详情	详情
(III)	30010	ethyl 4-(2,3,4-trimethoxybenzyl)-1-piperazinecarboxylate		C₁₇H₂₆N₂O₅	详情	详情
(IV)	24354	2,3-dimethoxy-4-(1-piperazinylmethyl)phenyl methyl ether		C₁₄H₂₂N₂O₃	详情	详情
(V)	30011	2-chloro-1-[4-(2,3,4-trimethoxybenzyl)-1-piperazinyl]-1-ethanone		C₁₆H₂₃ClN₂O₄	详情	详情
(VI)	30012	5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one	520-34-3	C₁₆H₁₂O₆	详情	详情

Extended Information