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【结 构 式】 
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【分子编号】62024 【品名】4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenyl methyl ether; 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene 【CA登记号】 |
【 分 子 式 】C17H18O3 【 分 子 量 】270.32812 【元素组成】C 75.53% H 6.71% O 17.76% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 4-methoxyphenyl iodide (I) with trimethylvinyllsilane (II) and 3,5-dimethoxyphenyl iodide (III) by means of Pd(dba)2, KF, tetrabutylammonium chloride (TBAC) and K2CO3 in toluene gives the trimethoxystilbene (IV), which is finally demethylated by reaction with BCl3 and tetrabutylammonium iodide (TBAI) in dichloromethane to afford the target Resveratrol.
| 【1】 Jeffery, T.; Ferber, B.; One-pot palladium-catalyzed highly chemo-, regio-, and stereoselective synthesis of trans-stilbene derivatives. A concise and convenient synthesis of resveratrol. Tetrahedron Lett 2003, 44, 1, 193. |
| 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) | 31009 | 1-iodo-4-methoxybenzene; 4-iodophenyl methyl ether | 696-62-8 | C7H7IO | 详情 | 详情 |
| (II) | 62022 | Vinyltrimethylsilane; Ethenyltrimethylsilane; Trimethylvinylsilane; TRIMETHYL(VINYL)SILANE; (Trimethylsilyl)ethylene; Vinyltrimethylsilane; Vinyl-trimethylsilan; (Trimethylsilyl)ethylene; (ETHENYLTRIMETHYLSILANE, TRIMETHYLVINYLSILANE) | 754-05-2 | C5H12Si | 详情 | 详情 |
| (III) | 62023 | 3-iodo-5-methoxyphenyl methyl ether; 1-iodo-3,5-dimethoxybenzene | C8H9IO2 | 详情 | 详情 | |
| (IV) | 62024 | 4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenyl methyl ether; 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene | C17H18O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)4-Methoxybenzyl bromide (I) is condensed with triphenylphosphine in refluxing toluene to produce the phosphonium salt (II). Subsequent Wittig condensation of (II) with 3,5-dimethoxybenzaldehyde (III) gives rise to a mixture of the title Z-stilbene and its E-isomer (IV), which can be separated by means of flash chromatography.
| 【1】 Pettit, G.R.; Grealish, M.P.; Jung, M.K.; Hamel, E.; Pettit, R.K.; Chapuis, J.-C.; Schmidt, J.M.; Antineoplastic agents. 465. Structural modification of resveratrol: Sodium resverastatin phosphate. J Med Chem 2002, 45, 12, 2534. |
| 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) | 27490 | 1-(bromomethyl)-4-methoxybenzene | C8H9BrO | 详情 | 详情 | |
| (II) | 64585 | (4-methoxybenzyl)(triphenyl)phosphonium bromide | C26H24BrOP | 详情 | 详情 | |
| (III) | 21720 | 3,5-dimethoxybenzaldehyde | 7311-34-4 | C9H10O3 | 详情 | 详情 |
| (IV) | 62024 | 4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenyl methyl ether; 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene | C17H18O3 | 详情 | 详情 |