5,6-dimethoxy-3,4-dihydro-2(1H)-naphthalenone -Drug Synthesis Database

【结构式】

【分子编号】37386

【品名】5,6-dimethoxy-3,4-dihydro-2(1H)-naphthalenone

【CA登记号】

【分子式】C₁₂H₁₄O₃

【分子量】206.24136

【元素组成】C 69.89% H 6.84% O 23.27%

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)

Nolomirole is synthesized by acylation of (rac)-6-(methylamino)-5,6,7,8-tetrahydronaphthalene-1,2-diol, CHF-1024 (I) with isobutyryl chloride (II) in THF. Reductocondensation of 5,6-dimethoxy-2-tetralone (III) with methylamine (IV) by means of LiBH4 or NaBH4 gives N-(5,6-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylamine (V), which is treated with 48% HBr at 110 C.

参考文献中间体

合成目标

【1】 Castaner, J.; Mealy, N.E.; Bayes, M.; Leeson, P.A.; Nolomirole Hydrochloride. Drugs Fut 2001, 26, 11, 1046.
【2】 Chiesi, P.; Villani, V. (Chiesi Farmaceutici SpA); 1,2,3,4-Tetrahydronaphthaline derivs., process for their preparation and pharmaceutical compsns. containing them. DE 3320936; GB 2123410 .

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)	49435	6-(methylamino)-5,6,7,8-tetrahydro-1,2-naphthalenediol		C₁₁H₁₅NO₂	详情	详情
(II)	14932	isobutyryl chloride; 2-methylpropanoyl chloride	79-30-1	C₄H₇ClO	详情	详情
(III)	37386	5,6-dimethoxy-3,4-dihydro-2(1H)-naphthalenone		C₁₂H₁₄O₃	详情	详情
(IV)	11021	Methanamine; Methylamine	74-89-5	CH₅N	详情	详情
(V)	37381	N-(5,6-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenyl)-N-methylamine; 5,6-dimethoxy-N-methyl-1,2,3,4-tetrahydro-2-naphthalenamine		C₁₃H₁₉NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIV)

Aminotetralin (VIII) was obtained by reductive amination of the 2-tetralone (XIV) in the presence of NaBH3CN.

参考文献中间体

合成目标

【1】 Chiesi, P.; Villani, V. (Chiesi Farmaceutici SpA); 1,2,3,4-Tetrahydronaphthaline derivs., process for their preparation and pharmaceutical compsns. containing them. DE 3320936; GB 2123410 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	11021	Methanamine; Methylamine	74-89-5	CH₅N	详情	详情
(VIII)	37381	N-(5,6-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenyl)-N-methylamine; 5,6-dimethoxy-N-methyl-1,2,3,4-tetrahydro-2-naphthalenamine		C₁₃H₁₉NO₂	详情	详情
(XIV)	37386	5,6-dimethoxy-3,4-dihydro-2(1H)-naphthalenone		C₁₂H₁₄O₃	详情	详情

Extended Information