1-phenyl-1,2-propanedione -Drug Synthesis Database

【结构式】

【分子编号】31481

【品名】1-phenyl-1,2-propanedione

【CA登记号】579-07-7

【分子式】C₉H₈O₂

【分子量】148.16132

【元素组成】C 72.96% H 5.44% O 21.6%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(II)

Condensation of 4,5-dichloro-1,2-phenylenediamine (I) with 1-phenyl-1,2-propanedione (II) in boiling AcOH provided quinoxaline (III). Subsequent reaction of (III) with ethyl bromopyruvate (IV) led to the pyrroloquinoxaline (V). After reduction of the ester group of (V) to alcohol (VI) with LiAlH4, further oxidation with MnO2 produced aldehyde (VII). This was condensed with boiling 3-(dimethylamino)propylamine (VIII), and the resulting imine (IX) was finally reduced to the target amine with NaBH4 in MeOH. The title compound was finally converted to the dioxalate salt upon treatment with oxalic acid in isopropanol.

参考文献中间体

合成目标

【1】 Guillon, J.; Rault, S.; Kervran, A.; Renard, P.; Manechez, D.; Pfeiffer, B.; Dallemagne, P.; Synthesis of new pyrrolo[1,2-a]quinoxalines: Potential non-peptide glucagon receptor antagonists. Eur J Med Chem 1998, 33, 4, 293.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	15713	Oxalic acid	144-62-7	C₂H₂O₄	详情	详情
(I)	18003	4,5-dichloro-1,2-benzenediamine; 4,5-Dichloro-o-phenylenediamine; 2-amino-4,5-dichlorophenylamine	5348-42-5	C₆H₆Cl₂N₂	详情	详情
(II)	31481	1-phenyl-1,2-propanedione	579-07-7	C₉H₈O₂	详情	详情
(III)	31482	6,7-dichloro-2-methyl-3-phenylquinoxaline		C₁₅H₁₀Cl₂N₂	详情	详情
(IV)	25183	ethyl 3-bromo-2-oxopropanoate;ethyl 3-bromopyruvate;Bromopyruvic acid ethyl ester;ethyl 3-bromopyruvate;ethyl bromopyruvate	70-23-5	C₅H₇BrO₃	详情	详情
(V)	31483	ethyl 7,8-dichloro-4-phenylpyrrolo[1,2-a]quinoxaline-2-carboxylate		C₂₀H₁₄Cl₂N₂O₂	详情	详情
(VI)	31484	(7,8-dichloro-4-phenylpyrrolo[1,2-a]quinoxalin-2-yl)methanol		C₁₈H₁₂Cl₂N₂O	详情	详情
(VII)	31486	7,8-dichloro-4-phenylpyrrolo[1,2-a]quinoxaline-2-carbaldehyde		C₁₈H₁₀Cl₂N₂O	详情	详情
(VIII)	25248	N-(3-aminopropyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,3-propanediamine	109-55-7	C₅H₁₄N₂	详情	详情
(IX)	31485	N(1)-[(E)-(7,8-dichloro-4-phenylpyrrolo[1,2-a]quinoxalin-2-yl)methylidene]-N(3),N(3)-dimethyl-1,3-propanediamine; N-[(E)-(7,8-dichloro-4-phenylpyrrolo[1,2-a]quinoxalin-2-yl)methylidene]-N-[3-(dimethylamino)propyl]amine		C₂₃H₂₂Cl₂N₄	详情	详情

Extended Information