6-Methoxy-2-naphthaldehyde -Drug Synthesis Database

【结构式】

【分子编号】29956

【品名】6-Methoxy-2-naphthaldehyde

【CA登记号】3453-33-6

【分子式】C₁₂H₁₀O₂

【分子量】186.2102

【元素组成】C 77.4% H 5.41% O 17.18%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

The condensation of 6-methoxy-2-naphthaldehyde (I) with ethyl aceto-acetate (II) gives ethyl 2-(6-methoxy-2-naphthylmethylene)acetoacetate (III), which is reduced to ethyl 2-(6-methoxy-2-naphthylmethyl)acetoacetate (IV). Finally, this compound is hydrolyzed and decarboxylated in acidic medium.

参考文献中间体

合成目标

【1】 Rose, C.J.; Miller, D. (SmithKline Beecham plc); A1 14777 by hydrogenation. CA 1134384 .

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)	29956	6-Methoxy-2-naphthaldehyde	3453-33-6	C₁₂H₁₀O₂	详情	详情
(II)	11819	ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate	141-97-9	C₆H₁₀O₃	详情	详情
(III)	29957	ethyl (Z)-2-acetyl-3-(6-methoxy-2-naphthyl)-2-propenoate		C₁₈H₁₈O₄	详情	详情
(IV)	29958	ethyl 2-[(6-methoxy-2-naphthyl)methyl]-3-oxobutanoate		C₁₈H₂₀O₄	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 of 6-methoxy-2-naphthaldehyde (I) with acetone by means of NaOH in water gives 4-(6-methoxy-2-naphtyl)-3-buten-2-one (II), which is reduced with H2 over Pd/C in ethyl acetate.

参考文献中间体

合成目标

【1】 Goudie, A.C. Ert al.; 4-(6-Methoxy-2-naphtyl)butan-2-one and related analogues, a novel structural class of antiinflammatory compounds. J Med Chem 1978, 21, 12, 1260.
【2】 Kyburz, E.; Aschwanden, W. (F. Hoffmann-La Roche AG); 1-(p-Methoxy-p-hydroxy, and p-benzyloxybenzoyl)-2-pyrrolidinones. DD 141828; EP 0005143; EP 0044088; ES 477587; ES 483756; JP 54117468 .
【3】 Neuman, M.; Blancafort, P.; Castaner, J.; Serradell, M.N.; Nabumetone. Drugs Fut 1981, 6, 1, 35.

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)	23199	2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether	67-64-1	C₃H₆O	详情	详情
(I)	29956	6-Methoxy-2-naphthaldehyde	3453-33-6	C₁₂H₁₀O₂	详情	详情
(II)	32194	(E)-4-(6-methoxy-2-naphthyl)-3-buten-2-one		C₁₅H₁₄O₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(V)

The bromination of beta-naphthol (I) gives the 1,6-dibromo-beta-naphthol (II), which is partially debrominated with Sn and BrH, yielding 1-bromo-beta-naphthol (III). The methylation of (III) with methanol/sulfuric acid affords the corresponding methyl ether (IV), which is treated with Mg and DMF to provide 6-methoxynaphthalene-2-carbaldehyde (V). The condensation of (V) with ethyl acetoacetate (VI) gives the expected adduct (VII), which is reduced with H2 over Pd/C to provide 2-acetyl-3-(6-methoxy-2-naphthyl)propionic acid ethyl ester (VIII). Finally, this compound is decarboxylated with aqueous HCl.

参考文献中间体

合成目标

【1】 Zhang, G.; et al.; A study on the synthesis of a new anti-inflammatory agent - nabumetone. J Shenyang Coll Pharm 1988, 5, 4, 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
(I)	44396	2-naphthol	135-19-3	C₁₀H₈O	详情	详情
(II)	44397	1,6-dibromo-2-naphthol	16239-18-2	C₁₀H₆Br₂O	详情	详情
(III)	44398	6-bromo-2-naphthol	15231-91-1	C₁₀H₇BrO	详情	详情
(IV)	44399	2-bromo-6-methoxynaphthalene; 6-bromo-2-naphthyl methyl ether	5111-65-9	C₁₁H₉BrO	详情	详情
(V)	29956	6-Methoxy-2-naphthaldehyde	3453-33-6	C₁₂H₁₀O₂	详情	详情
(VI)	11819	ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate	141-97-9	C₆H₁₀O₃	详情	详情
(VII)	29957	ethyl (Z)-2-acetyl-3-(6-methoxy-2-naphthyl)-2-propenoate		C₁₈H₁₈O₄	详情	详情
(VIII)	29958	ethyl 2-[(6-methoxy-2-naphthyl)methyl]-3-oxobutanoate		C₁₈H₂₀O₄	详情	详情

Extended Information