methyl 6-ethyl-4-hydroxy-2-octynoate -Drug Synthesis Database

【结构式】

【分子编号】57445

【品名】methyl 6-ethyl-4-hydroxy-2-octynoate

【CA登记号】

【分子式】C₁₁H₁₈O₃

【分子量】198.26212

【元素组成】C 66.64% H 9.15% O 24.21%

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：(IX)

Addition of the lithium acetylide prepared from methyl propiolate (VIII) to 3-ethylpentanal (VII) gives methyl 6-ethyl-4-hydroxy-2-octynoate (IX), which is further oxidized to the corresponding keto ester (X) employing the Jones reagent in acetone. Cycloaddition between alkyne (X) and the lithium derivative of the isobenzofuranone (V) gives rise to the 1,4-epoxy dihydronaphthalene adduct (XI). Subsequent acidic hydrolysis of (XI) furnishes the hydroxy naphthalenone (XII). Finally, reductive aromatization of (XII) using TiCl3 produces the title naphthol compound.

参考文献中间体

合成目标

【1】 Mori, S.; Takechi, S.; Kida, S. (Shionogi & Co. Ltd.); Process for producing lignan cpd.. EP 0646570; WO 9424087 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	57444	3-ethylpentanal		C₇H₁₄O	详情	详情
(VIII)	19588	methyl propiolate	922-67-8	C₄H₄O₂	详情	详情
(IX)	57445	methyl 6-ethyl-4-hydroxy-2-octynoate		C₁₁H₁₈O₃	详情	详情
(X)	57432	methyl 6-ethyl-4-oxo-2-octynoate		C₁₁H₁₆O₃	详情	详情
(XI)	57443	3-(3,4-dimethoxyphenyl)-4,5,6-trimethoxy-2-benzofuran-1(3H)-one		C₁₉H₂₀O₇	详情	详情
(XII)	57446	methyl 8-(3,4-dimethoxyphenyl)-10-(3-ethylpentanoyl)-4,5,6-trimethoxy-1-[(trimethylsilyl)oxy]-11-oxatricyclo[6.2.1.0~2,7~]undeca-2,4,6,9-tetraene-9-carboxylate		C₃₃H₄₄O₁₀Si	详情	详情

Extended Information