(E)-4-(6-methoxy-2-naphthyl)-3-buten-2-one -Drug Synthesis Database

【结构式】

【分子编号】32194

【品名】(E)-4-(6-methoxy-2-naphthyl)-3-buten-2-one

【CA登记号】

【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：(II)

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2

该中间体在本合成路线中的序号：(III)

The condensation of 2-bromo-6-methoxynaphthalene (I) with 3-buten-2-one (II) by means of PdCl2, PPh3 and K2CO3 in DMF at 132 C gives 4-(6-methoxy-2-naphthyl)-3-buten-2-one (III), which is then hydrogenated with H2 over Pd/C in DMF. The same condensation can be performed with PdCl2 , PPh3 and NaHCO3 in 1-methyl-2-pyrrolidone at 130 C. The reaction of 4-hydroxy-2-butanone (IV) with acetic anhydride or acetyl chloride gives 4-acetyl-2-butanone (V), which is condensed with 2-bromo-6-methoxynaphthalene (I) by means of PdCl2, PPh3 and K2CO3 in DMF at 132 C to yield the previously reported 4-(6-methoxy-2-naphthyl)-3-buten-2-one (III).

参考文献中间体

合成目标

【1】 Aslam, M.; et al.; Convenient synthesis of nabumetone. Synthesis 1989, 869.
【2】 Fritch, J.R.; Rios, D.E.; Smith, J.C.; Aslam, M. (Celanese AG); Use of 4-substd. 2-butanones to prepare nabumetone. WO 9640608 .

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)	44399	2-bromo-6-methoxynaphthalene; 6-bromo-2-naphthyl methyl ether	5111-65-9	C₁₁H₉BrO	详情	详情
(II)	30324	3-buten-2-one; methyl vinyl ketone	78-94-4	C₄H₆O	详情	详情
(III)	32194	(E)-4-(6-methoxy-2-naphthyl)-3-buten-2-one		C₁₅H₁₄O₂	详情	详情
(IV)	46053	4-hydroxy-2-butanone		C₄H₈O₂	详情	详情
(V)	46054	3-oxobutyl acetate		C₆H₁₀O₃	详情	详情

Extended Information