6-(4-Chlorophenyl)-4,6-dioxohexanoic acid -Drug Synthesis Database

【结构式】

【分子编号】12687

【品名】6-(4-Chlorophenyl)-4,6-dioxohexanoic acid

【CA登记号】

【分子式】C₁₂H₁₁ClO₄

【分子量】254.66964

【元素组成】C 56.6% H 4.35% Cl 13.92% O 25.13%

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)

A new synthesis of tepoxalin has been described: The condensation of 4-chloroacetophenone (I) with succinic anhydride (II) by means of lithium bis(trimethylsilyl)amide in THF at -20 C gives 6-(4-chlorophenyl)-4,6-dioxohexanoic acid (III), which is cyclized with 4-methoxyphenylhydrazine (IV) by means of triethylamine in methanol at room temperature to afford 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)pyrazol-3-yl]propanoic acid (V); finally this compound is condensed with methylhydroxylamine (VI) by means of oxalyl chloride and triethylamine at room temperature.

参考文献中间体

合成目标

【1】 Forerokelly, Y.; Murray, W.; Wachter, M.; Barton, D.; The regioselective synthesis of tepoxalin, 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-N-hydroxy-N-methylpropanamide and related 1,5-diarylpyrazole antiinflammatory agents. Synthesis 1991, 1, 1, 18.

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)	12685	4-Chloroacetophenone; 1-(4-Chlorophenyl)-1-ethanone; p-Chloroacetophenone	99-91-2	C₈H₇ClO	详情	详情
(II)	11291	Dihydro-2,5-furandione; Succinic anhydride	108-30-5	C₄H₄O₃	详情	详情
(III)	12687	6-(4-Chlorophenyl)-4,6-dioxohexanoic acid		C₁₂H₁₁ClO₄	详情	详情
(IV)	12688	4-Hydrazinophenyl methyl ether; 1-(4-Methoxyphenyl)hydrazine	3471-32-7	C₇H₁₀N₂O	详情	详情
(V)	12689	3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]propionic acid		C₁₉H₁₇ClN₂O₃	详情	详情
(VI)	12690	(Hydroxyamino)methane; N-Methylhydroxylamine	593-77-1	CH₅NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

A new method for the synthesis of tepoxalin has been reported: The cyclization of 6-(4-chlorophenyl)-4,6-dioxohexanoic acid (I) with refluxing acetic anhydride gives 5-[2-(4-chlorophenyl)-2-oxoethylidene]tetrahydrofuran-2-one (II), which is treated with methylhydroxylamine to afford the corresponding N-hydroxy-N-methylamide (III). Finally, this compound is cyclized with 4-methoxyphenylhydroazine (IV) by means of Na2CO3 in refluxing ethanol.

参考文献中间体

合成目标

【1】 Murray, W.V.; Hadden, S.K.; A facile synthesis of tepoxalin, 5-(4-chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-methyl-1H-pyrazole-3-propanamide. J Org Chem 1992, 57, 24, 6662.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	12690	(Hydroxyamino)methane; N-Methylhydroxylamine	593-77-1	CH₅NO	详情	详情
(I)	12687	6-(4-Chlorophenyl)-4,6-dioxohexanoic acid		C₁₂H₁₁ClO₄	详情	详情
(II)	12692	5-[(Z)-2-(4-Chlorophenyl)-2-oxoethylidene]dihydro-2-furanone		C₁₂H₉ClO₃	详情	详情
(III)	12693	6-(4-Chlorophenyl)-N-hydroxy-N-methyl-4,6-dioxohexanamide		C₁₃H₁₄ClNO₄	详情	详情
(IV)	12688	4-Hydrazinophenyl methyl ether; 1-(4-Methoxyphenyl)hydrazine	3471-32-7	C₇H₁₀N₂O	详情	详情

Extended Information