1-(4-chlorophenyl)-2-dihydro-2(3H)-furanylidene-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】45875

【品名】1-(4-chlorophenyl)-2-dihydro-2(3H)-furanylidene-1-ethanone

【CA登记号】

【分子式】C₁₂H₁₁ClO₂

【分子量】222.67084

【元素组成】C 64.73% H 4.98% Cl 15.92% O 14.37%

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：(VI)

Acetophenone (I) is condensed with gamma-butyrolactone (II) in the presence of NaOMe to afford compound (III), which is finally treated with BF3·Et2O and amine (IV) in dichloromethane/ether. Alternatively, the target compound can be synthesized by regioselective bromination of (III) with PBr3 in dichloromethane to yield bromo derivative (V) followed by heating with primary amine (IV) in MeOH. (Under forceful conditions (V) can be converted into intermediate (VI), which by heating in MeOH in the presence of primary amine (IV) can also lead to the desired product).

参考文献中间体

合成目标

【1】 Batra, S.; et al.; Syntheses and biological evaluation of 3-substituted amino-1-aryl-6-hydroxy-hex-2-ene-1-ones as antioxidant and hypolipidemic agents. Bioorg Med Chem 2000, 8, 8, 2195.

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)	20576	dihydro-2(3H)-furanone	96-48-0	C₄H₆O₂	详情	详情
(III)	45873	(Z)-1-(4-chlorophenyl)-3,6-dihydroxy-2-hexen-1-one		C₁₂H₁₃ClO₃	详情	详情
(IV)	12420	N-(2-Aminoethyl)-N,N-diethylamine; N,N-Diethylethylene-diamine; N(1),N(1)-Diethyl-1,2-ethanediamine	100-36-7	C₆H₁₆N₂	详情	详情
(V)	45874	(Z)-6-bromo-1-(4-chlorophenyl)-3-hydroxy-2-hexen-1-one		C₁₂H₁₂BrClO₂	详情	详情
(VI)	45875	1-(4-chlorophenyl)-2-dihydro-2(3H)-furanylidene-1-ethanone		C₁₂H₁₁ClO₂	详情	详情

Extended Information