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【结 构 式】

【分子编号】64828

【品名】1-[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]-1-ethanone

【CA登记号】

【 分 子 式 】C18H24O5

【 分 子 量 】320.38556

【元素组成】C 67.48% H 7.55% O 24.97%

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:(III)

Reaction of 2',5'-dihydroxyacetophenone (I) with dihydropyran (II) and pyridinium p-toluenesulfonate gives the protected bis-tetrahydropyranyl ether (III), which is submitted to Claisen-Schmidt condensation with 2-chlorobenzaldehyde (IV) in the presence of barium hydroxide, yielding the chalcone (V). Finally, the tetrahydropyranyl protecting groups of (V) are removed by acidic hydrolysis with p-toluenesulfonic acid in MeOH.

1 Nam, N.-H.; Kim, Y.; You, Y.-J.; Hong, D.-H.; Kim, H.-M.; Ahn, B.-Z.; Cytotoxic 2',5'-dihydroxychalcones with unexpected antiangiogenic activity. Eur J Med Chem 2003, 38, 2, 179.
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) 38479 1-(2,5-dihydroxyphenyl)-1-ethanone 490-78-8 C8H8O3 详情 详情
(II) 13684 3,4-Dihydro-2H-pyran;2,3-Dihydro-4H-pyran; 5,6-Dihydro-4H-pyran;Dihydropyran 110-87-2 C5H8O 详情 详情
(III) 64828 1-[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]-1-ethanone C18H24O5 详情 详情
(IV) 24114 2-chlorobenzaldehyde 89-98-5 C7H5ClO 详情 详情
(V) 64829 (E)-1-[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]-3-(2-chlorophenyl)-2-propen-1-one C25H27ClO5 详情 详情
Extended Information