5-hydroxy-7-[(3-methyl-2-butenyl)oxy]-2-phenyl-4H-chromen-4-one -Drug Synthesis Database

【结构式】

【分子编号】47708

【品名】5-hydroxy-7-[(3-methyl-2-butenyl)oxy]-2-phenyl-4H-chromen-4-one

【CA登记号】

【分子式】C₂₀H₁₈O₄

【分子量】322.36052

【元素组成】C 74.52% H 5.63% O 19.85%

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)

Alkylation of chrysin (I) with prenyl bromide (II) in the presence of K2CO3 in acetone provided 7-O-(3,3-dimethylallyl)chrysin (III). Claisen rearrangement of (III) in the presence of NaOAc in refluxing Ac2O gave rise to the 8-(1,1-dimethylallyl) flavone (IV) and minor amounts of the desired 8-(3,3-dimethylallyl) analogue (V). Saponification of the mixture of acetate esters, followed by chromatographic separation, furnished the title 8-(3,3-dimethylallyl)chrysin.

参考文献中间体

合成目标

【1】 Mariotte, A.-M.; Barron, D.; Syntheses of 8-C-(1,1-dimethylallyl) flavones and 3-methyl flavonols. Nat Prod Lett 1994, 4, 1, 21.

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)	47707	5,7-Dihydroxyflavone; Chrysin; Chrysine; 5,7-dihydroxy-2-phenyl-4H-chromen-4-one	480-40-0	C₁₅H₁₀O₄	详情	详情
(II)	12989	4-Bromo-2-methyl-2-butene; 1-Bromo-3-methyl-2-butene	870-63-3	C₅H₉Br	详情	详情
(III)	47708	5-hydroxy-7-[(3-methyl-2-butenyl)oxy]-2-phenyl-4H-chromen-4-one		C₂₀H₁₈O₄	详情	详情
(IV)	47709	5-(acetoxy)-8-(1,1-dimethyl-2-propenyl)-4-oxo-2-phenyl-4H-chromen-7-yl acetate		C₂₄H₂₂O₆	详情	详情
(V)	47710	5-(acetoxy)-8-(3-methyl-2-butenyl)-4-oxo-2-phenyl-4H-chromen-7-yl acetate		C₂₄H₂₂O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

In an improved procedure, chrysin (I) was alkylated with prenyl bromide (II) under phase-transfer conditions, and the resulting prenyl ether (III) was subsequently rearranged under microwave irradiation to produce a mixture of the title compound as the major product along with the 6-prenyl (VI) and the 6,8-diprenyl (VII) derivatives, which were separated by column chromatography.

参考文献中间体

合成目标

【1】 Conseil, G.; Daskiewicz, J.-B.; Bayet, C.; Viornery-Vanier, A.; Dmontet, C.; Di Pietro, A.; Comte, G.; Barron, D.; C-Isoprenylation of flavonoids enhances binding affinity toward P-glycoprotein and modulation of cancer cell chemoresistance. J Med Chem 2001, 44, 5, 763.

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)	47707	5,7-Dihydroxyflavone; Chrysin; Chrysine; 5,7-dihydroxy-2-phenyl-4H-chromen-4-one	480-40-0	C₁₅H₁₀O₄	详情	详情
(II)	12989	4-Bromo-2-methyl-2-butene; 1-Bromo-3-methyl-2-butene	870-63-3	C₅H₉Br	详情	详情
(III)	47708	5-hydroxy-7-[(3-methyl-2-butenyl)oxy]-2-phenyl-4H-chromen-4-one		C₂₀H₁₈O₄	详情	详情
(VI)	47711	5,7-dihydroxy-6-(3-methyl-2-butenyl)-2-phenyl-4H-chromen-4-one		C₂₀H₁₈O₄	详情	详情
(VII)	47712	5,7-dihydroxy-6,8-bis(3-methyl-2-butenyl)-2-phenyl-4H-chromen-4-one		C₂₅H₂₆O₄	详情	详情

Extended Information