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【结 构 式】 
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【分子编号】44364 【品名】3-methoxy-5-(methylsulfonyl)-4-propoxybenzaldehyde 【CA登记号】 |
【 分 子 式 】C12H16O5S 【 分 子 量 】272.32204 【元素组成】C 52.93% H 5.92% O 29.38% S 11.78% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 3,4,5-trimethoxyacetophenone (I) with diethylamine and formaldehyde gives 3-(dimethylamino)-1-(3,4,5-trimethoxyphenyl)-1-propanone (II), which is treated with methyl iodide at 80 C to yield 1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (III). The condensation of (III) with 3-methoxy-5-(methylsulfonyl)-4-propoxybenzaldehyde (IV) by means of TEA and the thiazolium derivative (V) affords the asymmetric butane-1,4-dione (VI), which is reduced with LiAlH4 or NaBH4 to provide the (RS,RS)-butane-1,4-diol (VIII). Finally, this compound is dehydrated to the target tetrahydrofuran by means of TFA, PdCl2/Cu(NO3)2 or MsCl/pyridine.
| 【1】 Biftu, T.; Chabala, J.C.; Acton, J.; Kuo, C.-H.; Stevenson, R.; 2,5-DIARYLTETRAHYDROFURANS: PAF ANTAGONISTS. Drugs Fut 1989, 14, 4, 359. |
| 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) | 44362 | 1-(3,4,5-trimethoxyphenyl)-1-ethanone | 1136-86-3 | C11H14O4 | 详情 | 详情 |
| (II) | 44363 | 3-(dimethylamino)-1-(3,4,5-trimethoxyphenyl)-1-propanone | C14H21NO4 | 详情 | 详情 | |
| (III) | 27941 | 1-(3,4,5-trimethoxyphenyl)-2-propen-1-one | C12H14O4 | 详情 | 详情 | |
| (IV) | 44364 | 3-methoxy-5-(methylsulfonyl)-4-propoxybenzaldehyde | C12H16O5S | 详情 | 详情 | |
| (V) | 44365 | 3,4-diethyl-5-(2-hydroxyethyl)-1,3-thiazol-3-ium bromide | C9H16BrNOS | 详情 | 详情 | |
| (VI) | 44366 | 1-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione | C24H30O9S | 详情 | 详情 | |
| (VII) | 44367 | 4-hydroxy-4-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-1-butanone | C24H32O9S | 详情 | 详情 | |
| (VIII) | 44368 | (1R,4R)-1-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-4-(3,4,5-trimethoxyphenyl)-1,4-butanediol | C24H34O9S | 详情 | 详情 |