3,4-Dihydro-2(1H)-naphthalenone; beta-Tetralone -Drug Synthesis Database

【结构式】

【分子编号】39106

【品名】3,4-Dihydro-2(1H)-naphthalenone; beta-Tetralone

【CA登记号】530-93-8

【分子式】C₁₀H₁₀O

【分子量】146.1888

【元素组成】C 82.16% H 6.89% O 10.94%

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 reaction of beta-tetralone (I) with pyrrolidine (A) yields enamine (II), which is condensed with phenacyl bromide (B) in DMF to give the 1-phenacyl-2-tetralone (III). Finally, this diketone is cyclized with 5-aminosalycilic acid (C) in refluxing acetic acid.

参考文献中间体

合成目标

【1】 Anderson, V.B.; et al.; Carboxyarylindoles as non steroidal anti-inflammatory agents. J Med Chem 1976, 1, 7, 320.
【2】 Castaner, J.; Arrigoni-Martelli, E.; Fendosal. Drugs Fut 1976, 1, 7, 320.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	10315	2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone	70-11-1	C₈H₇BrO	详情	详情
(A)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(I)	39106	3,4-Dihydro-2(1H)-naphthalenone; beta-Tetralone	530-93-8	C₁₀H₁₀O	详情	详情
(II)	20382	1-(3,4-dihydro-2-naphthalenyl)pyrrolidine	21403-95-2	C₁₄H₁₇N	详情	详情
(III)	40460	1-(2-oxo-2-phenylethyl)-3,4-dihydro-2(1H)-naphthalenone		C₁₈H₁₆O₂	详情	详情
(C)	29932	5-amino-2-hydroxybenzoic acid	89-57-6	C₇H₇NO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The condensation beta-tetralone (I) with phenyl 4-methoxybenzoate (II) by means of NaNH2 in THF gives 3,4-dihydro-1-(4-methoxybenzoyl)-2(1H)-naphthalenone (III), which is then submitted to a Grignard reaction with 4-methoxyphenylmagnesium bromide (IV) in hot THF yielding 3,4-dihydro-2-(4-methoxyphenyl)-1-naphthyl-4-methoxyphenyl ketone (V). The cleavage of one methoxy group of (V) with sodium ethylmercaptide (A) in dry DMF affords 3,4-dihydro-2-(4-methoxyphenyl)-1-naphthyl-4-hydroxyphenyl ketone (VI), which is finally condensed with N-(2-chloroethyl)pyrrolidine (VII) by means of K2CO3 in refluxing 2-butanone.

参考文献中间体

合成目标

【1】 Jones, C.D.; et al.; Synthesis and antiestrogenic activity of [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl][4-[2-(1-pyrrolidinyl)ethoxyphenyl]methanone]methane sulfonic acid salt. J Med Chem 1979, 22, 8, 962-966.
【2】 Castaner, J.; Hillier, K.; Trioxifene mesylate. Drugs Fut 1980, 5, 5, 259.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	39110	Sodium 1-ethanethiolate; Sodium ethylmercaptide	811-51-8	C₂H₅NaS	详情	详情
(I)	39106	3,4-Dihydro-2(1H)-naphthalenone; beta-Tetralone	530-93-8	C₁₀H₁₀O	详情	详情
(II)	39107	Phenyl 4-methoxybenzoate		C₁₄H₁₂O₃	详情	详情
(III)	39108	1-(4-Methoxybenzoyl)-3,4-dihydro-2(1H)-naphthalenone; 3,4-Dihydro-1-(4-methoxybenzoyl)-2(1H)-naphthalenone		C₁₈H₁₆O₃	详情	详情
(IV)	37674	Bromo(4-methoxyphenyl)magnesium; 4-Methoxyphenylmagnesium bromide	352-13-6	C₇H₇BrMgO	详情	详情
(V)	39109	(4-Methoxyphenyl)[2-(4-methoxyphenyl)-3,4-dihydro-1-naphthalenyl]methanone; 3,4-Dihydro-2-(4-methoxyphenyl)-1-naphthyl-4-methoxyphenyl ketone		C₂₅H₂₂O₃	详情	详情
(VI)	39111	(4-Hydroxyphenyl)[2-(4-methoxyphenyl)-3,4-dihydro-1-naphthalenyl]methanone; 3,4-Dihydro-2-(4-methoxyphenyl)-1-naphthyl-4-hydroxyphenyl ketone		C₂₄H₂₀O₃	详情	详情
(VII)	33922	1-(2-Chloroethyl)pyrrolidine; N-(2-Chloroethyl)pyrrolidine		C₆H₁₂ClN	详情	详情

Extended Information