4-formyl-2,6-bis(1-methylethyl)phenyl acetate -Drug Synthesis Database

【结构式】

【分子编号】63372

【品名】4-formyl-2,6-bis(1-methylethyl)phenyl acetate

【CA登记号】

【分子式】C₁₅H₂₀O₃

【分子量】248.322

【元素组成】C 72.55% H 8.12% O 19.33%

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：(VII)

3,5-Diisopropyl-4-hydroxybenzaldehyde (VI) is esterified with acetyl chloride, producing acetate (VII). Subsequent Wittig condensation of aldehyde (VII) with carboethoxymethylene triphenylphosphorane leads to the cinnamyl derivative (VIII), which is further hydrogenated to the arylpropionic ester (IX). After saponification of ester (IX) with LiOH, the resultant carboxylic acid (X) is coupled to amine (V), producing amide (XI). Finally, amide reduction with borane in THF gives rise to the target amine.

参考文献中间体

合成目标

【1】 Auvin, S.; Auget, M.; Navet, E.; Harnett, J.J.; Viossat, I.; Schulz, J.; Bigg, D.; Chabrier, P.-E.; Novel inhibitors of neuronal nitric oxide synthase with potent antioxidant properties. Bioorg Med Chem Lett 2003, 13, 2, 209.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	14182	ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane	1099-45-2	C₂₂H₂₁O₂P	详情	详情
(V)	63370	N-[3-(aminomethyl)phenyl]-2-thiophenecarboximidamide		C₁₂H₁₃N₃S	详情	详情
(VI)	63371	4-hydroxy-3,5-bis(1-methylethyl)benzaldehyde		C₁₃H₁₈O₂	详情	详情
(VII)	63372	4-formyl-2,6-bis(1-methylethyl)phenyl acetate		C₁₅H₂₀O₃	详情	详情
(VIII)	63373	ethyl 3-[4-(acetyloxy)-3,5-bis(1-methylethyl)phenyl]-2-propenoate		C₁₉H₂₆O₄	详情	详情
(IX)	63374	ethyl 3-[4-(acetyloxy)-3,5-bis(1-methylethyl)phenyl]propanoate		C₁₉H₂₈O₄	详情	详情
(X)	63375	3-[4-hydroxy-3,5-bis(1-methylethyl)phenyl]propanoic acid		C₁₅H₂₂O₃	详情	详情
(XI)	63376	3-[4-hydroxy-3,5-bis(1-methylethyl)phenyl]-N-[(3-{[imino(2-thiophenyl)methyl]amino}phenyl)methyl]propanamide		C₂₇H₃₃N₃O₂S	详情	详情

Extended Information