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【结 构 式】 
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【分子编号】56080 【品名】4-(4-hydroxybenzyl)-7-methoxy-3-phenyl-2H-chromen-2-one 【CA登记号】 |
【 分 子 式 】C23H18O4 【 分 子 量 】358.39352 【元素组成】C 77.08% H 5.06% O 17.86% |
合成路线1
该中间体在本合成路线中的序号：(VI)Friedel-Crafts acylation of 3-methoxyphenol (I) with 4-hydroxyphenylacetic acid (II) in the presence of ZnCl2 and POCl3 furnished ketone (III), which was subsequently protected with triisopropylsilyl chloride and Et3N to yield the mono-silyl ether (IV). Coumarin (VI) was then synthesized by condensation of hydroxy ketone (IV) with phenylacetyl chloride (V) in the presence of K2CO3. Alkylation of the phenolic hydroxyl group of (VI) with N-(2-chloroethyl)piperidine (VII) gave the piperidinylethyl ether (VIII). Finally, selective methyl ether hydrolysis using HBr in refluxing HOAc led to the title compound.
| 【1】 Bhagwat, S.S.; McKie, J.A.; Khammungkhune, S. (Signal Pharmaceuticals, Inc.); Cpds. and methods for modulation of estrogen receptors. WO 0149673 . |
| 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) | 22389 | 3-Methoxyphenol | 150-19-6 | C7H8O2 | 详情 | 详情 |
| (II) | 18430 | 2-(4-Hydroxyphenyl)acetic acid; 4-Hydroxyphenylacetic acid | 156-38-7 | C8H8O3 | 详情 | 详情 |
| (III) | 56078 | 1-(2-hydroxy-4-methoxyphenyl)-2-(4-hydroxyphenyl)-1-ethanone | C15H14O4 | 详情 | 详情 | |
| (IV) | 56079 | 1-(2-hydroxy-4-methoxyphenyl)-2-{4-[(triisopropyl-lambda~4~-sulfanyl)oxy]phenyl}-1-ethanone | C24H34O4S | 详情 | 详情 | |
| (V) | 25890 | 2-phenylacetyl chloride；Phenylacetyl chloride;Phenacetyl chloride;Benzeneacetyl chloride | 103-80-0 | C8H7ClO | 详情 | 详情 |
| (VI) | 56080 | 4-(4-hydroxybenzyl)-7-methoxy-3-phenyl-2H-chromen-2-one | C23H18O4 | 详情 | 详情 | |
| (VII) | 10117 | 1-(2-Chloroethyl)piperidine; N-(2-Chloroethyl)piperidine | 1932-03-2 | C7H14ClN | 详情 | 详情 |
| (VIII) | 56081 | 7-methoxy-3-phenyl-4-{4-[2-(1-piperidinyl)ethoxy]benzyl}-2H-chromen-2-one | C30H31NO4 | 详情 | 详情 |