(E)-3-benzyl-4-oxo-2-pentenoic acid -Drug Synthesis Database

【结构式】

【分子编号】46968

【品名】(E)-3-benzyl-4-oxo-2-pentenoic acid

【CA登记号】

【分子式】C₁₂H₁₂O₃

【分子量】204.22548

【元素组成】C 70.57% H 5.92% O 23.5%

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：(I)

Oxazinone (II) was prepared by cyclization of the unsaturated keto acid (I) with hydroxylamine. Subsequent radical bromination of (II) with N-bromosuccinimide (NBS) provided the alpha-bromobenzyl derivative (III). Alkylation of 3-chlorophenyl piperazine (IV) with N-(2-bromoethyl)phthalimide (V) gave adduct (VI). Further hydrazinolysis of the phthaloyl group of (VI) yielded the primary amine (VII). Finally, condensation between bromide (III) and amine (VII) in refluxing THF furnished the title 5-amino oxazinone derivative.

参考文献中间体

合成目标

【1】 Rubat, C.; Bebot, M.; Fialip, J.; Coudert, P.; Courteix, C.; Couquelet, J.; Synthesis and analgesic effects of 5-[4-(arylpiperazin-1-yl)alkylamino]-4-benzyl-3-methyl-1,2-oxazin-6-ones. Arzneim-Forsch Drug Res 2000, 50, 4, 353.

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)	46968	(E)-3-benzyl-4-oxo-2-pentenoic acid		C₁₂H₁₂O₃	详情	详情
(II)	46969	4-benzyl-3-methyl-6H-1,2-oxazin-6-one		C₁₂H₁₁NO₂	详情	详情
(III)	46970	4-[bromo(phenyl)methyl]-3-methyl-6H-1,2-oxazin-6-one		C₁₂H₁₀BrNO₂	详情	详情
(IV)	37025	2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione	574-98-1	C₁₀H₈BrNO₂	详情	详情
(V)	22114	1-(3-chlorophenyl)piperazine	6640-24-0	C₁₀H₁₃ClN₂	详情	详情
(VI)	46971	2-[2-[4-(3-chlorophenyl)-1-piperazinyl]ethyl]-1H-isoindole-1,3(2H)-dione		C₂₀H₂₀ClN₃O₂	详情	详情
(VII)	46972	2-[4-(3-chlorophenyl)-1-piperazinyl]-1-ethanamine; 2-[4-(3-chlorophenyl)-1-piperazinyl]ethylamine		C₁₂H₁₈ClN₃	详情	详情

Extended Information