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【结 构 式】 
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【分子编号】26359 【品名】methyl (E)-4-(2,5-dihydroxy-3,4,6-trimethylphenyl)-2-butenoate 【CA登记号】 |
【 分 子 式 】C14H18O4 【 分 子 量 】250.29452 【元素组成】C 67.18% H 7.25% O 25.57% |
合成路线1
该中间体在本合成路线中的序号：(III)Raxofelast has been synthesized by a short route involving Friedel-Crafts alkylation of trimethylhydroquinone (I) by methyl 4-bromocrotonate (II). The crude reaction mixture containing methyl 4-(2,5-dihydroxy-3,4,6-trimethylphenyl)-2(E)-butenoate (III) was directly submitted to a hydrolytic cyclization in alkaline environment in the presence of a strong reducing agent to afford (±)-2,3-dihydro-5-hydroxy-4,6,7-trimethyl-2-benzofuranacetic acid (IV) (IRFI-005). Acetylation of phenolic hydroxyl by routine methods, followed by recrystallization by isopropyl acetate, gave the final product.
| 【1】 De Vellis, P.; Scuri, R.; Zanarella, S.; Ceccarelli, S.; Synthesis of novel 2-substituted 5-oxycoumarans via a direct route to 2,3-dihydro-5-hydroxy-2-benzofuranacetic acids. J Heterocycl Chem 1993, 30, 679. |
| 【2】 Cuzzocrea, S.; Ceccarelli, S.; Raxofelast. Drugs Fut 1999, 24, 7, 735. |
| 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) | 26357 | 2,3,5-trimethyl-1,4-benzenediol | 700-13-0 | C9H12O2 | 详情 | 详情 |
| (II) | 26358 | methyl (E)-4-bromo-2-butenoate | 1117-71-1 | C5H7BrO2 | 详情 | 详情 |
| (III) | 26359 | methyl (E)-4-(2,5-dihydroxy-3,4,6-trimethylphenyl)-2-butenoate | C14H18O4 | 详情 | 详情 | |
| (IV) | 26360 | 2-(5-hydroxy-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-2-yl)acetic acid | C13H16O4 | 详情 | 详情 | |
| (V) | 26361 | methyl (E)-2-butenoate | 623-43-8 | C5H8O2 | 详情 | 详情 |