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【结 构 式】 
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【分子编号】57446 【品名】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 【CA登记号】 |
【 分 子 式 】C33H44O10Si 【 分 子 量 】628.79186 【元素组成】C 63.04% H 7.05% O 25.44% Si 4.47% |
合成路线1
该中间体在本合成路线中的序号：(XII)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.
| 【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 |