6-methoxy-2-phenyl-3,4-dihydro-1(2H)-naphthalenone -Drug Synthesis Database

【结构式】

【分子编号】39795

【品名】6-methoxy-2-phenyl-3,4-dihydro-1(2H)-naphthalenone

【CA登记号】

【分子式】C₁₇H₁₆O₂

【分子量】252.31284

【元素组成】C 80.93% H 6.39% O 12.68%

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：(VII)

The condensation of 3-methoxyacetophenone (I) with benzaldehyde (II) by means of NaOH in ethanol - water gives 3'-methoxychalcone (III), which by addition of HCN (KCN) in ethanol-acetic acid is transformed into 2-phenyl-4-(3-methoxyphenyl)-4-oxobutyronitrile (IV). The hydrolysis of (IV) with aqueous H2SO4 at 100 C affords the corresponding ketoacid (V), which is reduced with amalgamated zinc and 2N HCl yielding 2-phenyl-4-(3-methoxyphenyl)butyric acid (VI). The cyclization of (VI) by means of liquid HF yields 2-phenyl-6-methoxy-1,2,3,4-tetrahydro-1-naphthalenone (VII), which is finally condensed with 4-(2-pyrrolidinoethoxy)phenylmagnesium bromide in refluxing THF.

参考文献中间体

合成目标

【1】 Thorpe, P.; Castañer, J.; Nafoxidine. Drugs Fut 1978, 3, 3, 211.
【2】 Duncan, G.W.; Lednicer, D.; US 3483293 .
【3】 Lednicer, D.; US 3274213 .

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)	18792	3-methoxyacetophenone; 1-(3-methoxyphenyl)-1-ethanone	586-37-8	C₉H₁₀O₂	详情	详情
(II)	10498	Benzaldehyde;Benzoic aldehyde;Phenylmethanal	100-52-7	C₇H₆O	详情	详情
(III)	39791	(E)-1-(3-methoxyphenyl)-3-phenyl-2-propen-1-one		C₁₆H₁₄O₂	详情	详情
(IV)	39792	4-(3-methoxyphenyl)-4-oxo-2-phenylbutanenitrile		C₁₇H₁₅NO₂	详情	详情
(V)	39793	4-(3-methoxyphenyl)-4-oxo-2-phenylbutyric acid		C₁₇H₁₆O₄	详情	详情
(VI)	39794	4-(3-methoxyphenyl)-2-phenylbutyric acid		C₁₇H₁₈O₃	详情	详情
(VII)	39795	6-methoxy-2-phenyl-3,4-dihydro-1(2H)-naphthalenone		C₁₇H₁₆O₂	详情	详情
(VIII)	29184	bromo[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]magnesium		C₁₂H₁₆BrMgNO	详情	详情

Extended Information