5-(acetoxy)-8-(1,1-dimethyl-2-propenyl)-4-oxo-2-phenyl-4H-chromen-7-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】47709

【品名】5-(acetoxy)-8-(1,1-dimethyl-2-propenyl)-4-oxo-2-phenyl-4H-chromen-7-yl acetate

【CA登记号】

【分子式】C₂₄H₂₂O₆

【分子量】406.43508

【元素组成】C 70.92% H 5.46% O 23.62%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

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

Extended Information