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【结 构 式】 
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【分子编号】60609 【品名】4-[3-(benzyloxy)-5-fluorophenyl]-4-methoxytetrahydro-2H-pyran; benzyl 3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenyl ether 【CA登记号】 |
【 分 子 式 】C19H21FO3 【 分 子 量 】316.3723432 【元素组成】C 72.13% H 6.69% F 6.01% O 15.17% |
合成路线1
该中间体在本合成路线中的序号：(XI)Displacement of 3,5-difluorobromobenzene (VII) with the sodium alkoxide of benzyl alcohol yields the benzyl ether (VIII). Metalation of (VIII) with butyllithium, followed by addition to tetrahydropyran-4-one (IX) furnishes the carbinol adduct (X). This is converted to the methyl ether (XI) by alkylation with iodomethane in the presence of NaH. Then, hydrogenolysis of the O-benzyl group of (XI) over Pd(OH)2 provides phenol (XII). Finally, condensation between phenol (XII) and mesylate (VI) gives rise to the title compound
| 【1】 Barbey, S.; et al.; Synthesis and activity of a new methoxytetrahydropyran derivative as dual cyclooxygenase-2/5-lipoxygenase inhibitor. Bioorg Med Chem Lett 2002, 12, 5, 779. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 60606 | {1-[4-(methylsulfonyl)phenyl]-5-phenyl-1H-pyrazol-3-yl}methyl methanesulfonate | C18H18N2O5S2 | 详情 | 详情 | |
| (VII) | 30794 | 1-bromo-3,5-difluorobenzene | 461-96-1 | C6H3BrF2 | 详情 | 详情 |
| (VIII) | 60607 | 1-(benzyloxy)-3-bromo-5-fluorobenzene; benzyl 3-bromo-5-fluorophenyl ether | C13H10BrFO | 详情 | 详情 | |
| (IX) | 31563 | tetrahydro-4H-pyran-4-one | 29943-42-8 | C5H8O2 | 详情 | 详情 |
| (X) | 60608 | 4-[3-(benzyloxy)-5-fluorophenyl]tetrahydro-2H-pyran-4-ol | C18H19FO3 | 详情 | 详情 | |
| (XI) | 60609 | 4-[3-(benzyloxy)-5-fluorophenyl]-4-methoxytetrahydro-2H-pyran; benzyl 3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenyl ether | C19H21FO3 | 详情 | 详情 | |
| (XII) | 60610 | 3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenol | C12H15FO3 | 详情 | 详情 |