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【结 构 式】 
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【分子编号】60512 【品名】3,4,5-trimethoxyphenylboronic acid 【CA登记号】 |
【 分 子 式 】C9H13BO5 【 分 子 量 】212.01022 【元素组成】C 50.99% H 6.18% B 5.1% O 37.73% |
合成路线1
该中间体在本合成路线中的序号：(XVI)In a different synthetic strategy, the required dibromostyrene (XIV) was prepared in low yield by Wittig-like condensation of 3-hydroxy-4-methoxybenzaldehyde (XII) with carbon tetrabromide in the presence of PPh-3. In an improved process, the phenolic hydroxyl of (XII) was first protected as the silyl ether (X), which was then condensed with CBr4/PPh3 to give (XIII). Subsequent desilylation of (XIII) with tetrabutylammonium fluoride provided (XIV). Stereoselective debromination of the dibromostyrene (XIV) with tributyltin hydride and tetrakis(triphenylphosphine)palladium(0) led to the Z-bromostyrene (XV). This was finally subjected to a palladium-catalyzed Suzuki coupling with 3,4,5-trimethoxybenzeneboronic acid (XVI) to furnish the title Z-olefin as the major isomer
| 【1】 Gaukroger, K.; Hadfield, J.A.; Hepworth, L.A.; Lawrence, N.J.; McGrown, A.T.; Novel synthesis of cis and trans isomers of combretastatin A-4. J Org Chem 2001, 66, 24, 8135. |
| 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) | 60505 | 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol | 117048-60-9 | C18H20O5 | 详情 | 详情 |
| (X) | 26114 | 3-[[tert-butyl(dimethyl)silyl]oxy]-4-methoxybenzaldehyde | C14H22O3Si | 详情 | 详情 | |
| (XII) | 18455 | 3-hydroxy-4-methoxybenzaldehyde; Isovanillin | 621-59-0 | C8H8O3 | 详情 | 详情 |
| (XIII) | 60509 | tert-butyl(dimethyl)silyl 5-(2,2-dibromovinyl)-2-methoxyphenyl ether; tert-butyl[5-(2,2-dibromovinyl)-2-methoxyphenoxy]dimethylsilane | C15H22Br2O2Si | 详情 | 详情 | |
| (XIV) | 60510 | 5-(2,2-dibromovinyl)-2-methoxyphenol | C9H8Br2O2 | 详情 | 详情 | |
| (XV) | 60511 | 5-[(Z)-2-bromoethenyl]-2-methoxyphenol | C9H9BrO2 | 详情 | 详情 | |
| (XVI) | 60512 | 3,4,5-trimethoxyphenylboronic acid | C9H13BO5 | 详情 | 详情 |