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【结 构 式】 
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【分子编号】44369 【品名】1-(3-iodo-5-methoxy-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione 【CA登记号】 |
【 分 子 式 】C23H27IO7 【 分 子 量 】542.36765 【元素组成】C 50.93% H 5.02% I 23.4% O 20.65% |
合成路线1
该中间体在本合成路线中的序号：(VI)The alkylation of 4-hydroxy-3-iodo-5-methoxybenzaldehyde (I) with propyl bromide (II) by means of K2CO3 in hot DMF gives the propyl ether (III), which is condensed with 3-(dimethylamino)-1-(3,4,5-trimethoxyphenyl)-1-propanone (IV) (obtained by reaction of 3,4,5-trimethoxyacetophenone (V) with dimethylamine and formaldehyde), yielding the asymmetric butanedione (VI). The reaction of (VI) with dimethyl disulfide by means of Cu at 160 C affords the methylsulfanyl compound (VII), which is oxidized with MCPBA in dichloromethane to provide the sulfone derivative (VIII). The reduction of the butanedione (VIII) with NaBH4 in hot ethanol gives the (RS,RS)-diol (IX), which is finally cyclized by means of TFA in chloroform.
| 【1】 Ponpipom, M.M.; Hwang, S.B.; Doebber, T.W.; Acton, J.J.; Alberts, A.W.; Biftu, T.; Brooker, D.R.; Bugianesi, R.L.; Chabala, J.C.; Gamble, N.L.; et al.; (±)-trans-2-(3-Methoxy-5-methylsulfonyl-4-propoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (L-659,989), a novel, potent PAF receptor antagonist. Biochem Biophys Res Commun 1988, 150, 3, 1213. |
| 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) | 12758 | 4-Hydroxy-3-iodo-5-methoxybenzaldehyde; 5-Iodovanillin | 5438-36-8 | C8H7IO3 | 详情 | 详情 |
| (II) | 19502 | Propyl bromide; 1-Bromopropane | 106-94-5 | C3H7Br | 详情 | 详情 |
| (III) | 12759 | 3-Iodo-5-methoxy-4-propoxybenzaldehyde | C11H13IO3 | 详情 | 详情 | |
| (IV) | 44362 | 1-(3,4,5-trimethoxyphenyl)-1-ethanone | 1136-86-3 | C11H14O4 | 详情 | 详情 |
| (V) | 44363 | 3-(dimethylamino)-1-(3,4,5-trimethoxyphenyl)-1-propanone | C14H21NO4 | 详情 | 详情 | |
| (VI) | 44369 | 1-(3-iodo-5-methoxy-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione | C23H27IO7 | 详情 | 详情 | |
| (VII) | 44370 | 1-[3-methoxy-5-(methylsulfanyl)-4-propoxyphenyl]-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione | C24H30O7S | 详情 | 详情 | |
| (VIII) | 44366 | 1-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione | C24H30O9S | 详情 | 详情 | |
| (IX) | 44368 | (1R,4R)-1-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-4-(3,4,5-trimethoxyphenyl)-1,4-butanediol | C24H34O9S | 详情 | 详情 |