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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information