1-[4-(benzyloxy)phenyl]-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】36423

【品名】1-[4-(benzyloxy)phenyl]-1-ethanone

【CA登记号】54696-05-8

【分子式】C₁₅H₁₄O₂

【分子量】226.27496

【元素组成】C 79.62% H 6.24% O 14.14%

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：(VI)

The bromination of 4-benzyloxyacetophenone (VI) with Br2 in dioxane gives 4-benzyloxyphenacyl bromide (VII), which by reduction with NaBH4 in dioxane and epoxidation with NaOH water is converted into (I). The condensation of 4-benzyloxystyrene oxide (I) with 1,1-dimethyl-3-(2-methoxyphenyl)propylamine (II) in refluxing isopropanol gives 1-(4-benzyloxyphenyl)-2-[1,1-dimethyl-3-(2-methoxyphenyl)propylamino]ethanol (III), which is debenzylated by reduction with H2 over Pd/C in ethanol, and treated with HCl.

参考文献中间体

合成目标

【1】 Olsson, O.A.T.; Persson, N.H.A.; Svensson, L.A.; Waldeck, C.B.; Wetterlin, K.J.L.; EP 0004835 .
【2】 Castaner, J.; Blancafort, P.; Serradell, M.N.; D-2343. Drugs Fut 1982, 7, 1, 17.

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)	36425	2-[4-(benzyloxy)phenyl]oxirane; benzyl 4-(2-oxiranyl)phenyl ether		C₁₅H₁₄O₂	详情	详情
(II)	36422	3-(2-methoxyphenyl)-1,1-dimethylpropylamine; 4-(2-methoxyphenyl)-2-methyl-2-butanamine		C₁₂H₁₉NO	详情	详情
(III)	36426	1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]amino]-1-ethanol		C₂₇H₃₃NO₃	详情	详情
(VI)	36423	1-[4-(benzyloxy)phenyl]-1-ethanone	54696-05-8	C₁₅H₁₄O₂	详情	详情
(VII)	36424	1-[4-(benzyloxy)phenyl]-2-bromo-1-ethanone		C₁₅H₁₃BrO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

The oxidation of (VI) with SeO2 in hot dioxane-water gives 4-benzyloxyphenylglyoxal (IV). The condensation with (II) in refluxing ethanol, gives 4-benzyloxy-alpha-[1,1-dimethyl-3-(2-methoxyphenyl)propylimino]acetophenone (V), which is then reduced with NaBH4 in ethanol to afford (III), which is debenzylated by reduction with H2 over Pd/C in ethanol, and treated with HCl.

参考文献中间体

合成目标

【1】 Olsson, O.A.T.; Persson, N.H.A.; Svensson, L.A.; Waldeck, C.B.; Wetterlin, K.J.L.; EP 0004835 .
【2】 Castaner, J.; Blancafort, P.; Serradell, M.N.; D-2343. Drugs Fut 1982, 7, 1, 17.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	36422	3-(2-methoxyphenyl)-1,1-dimethylpropylamine; 4-(2-methoxyphenyl)-2-methyl-2-butanamine		C₁₂H₁₉NO	详情	详情
(III)	36426	1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]amino]-1-ethanol		C₂₇H₃₃NO₃	详情	详情
(IV)	31696	2-[4-(benzyloxy)phenyl]-2-oxoacetaldehyde; 4-benzyloxy-alpha-oxophenylacetaldehyde		C₁₅H₁₂O₃	详情	详情
(V)	36427	1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]imino]-1-ethanone		C₂₇H₂₉NO₃	详情	详情
(VI)	36423	1-[4-(benzyloxy)phenyl]-1-ethanone	54696-05-8	C₁₅H₁₄O₂	详情	详情

Extended Information