(E)-1-[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]-3-(2-chlorophenyl)-2-propen-1-one -Drug Synthesis Database

【结构式】

【分子编号】64829

【品名】(E)-1-[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]-3-(2-chlorophenyl)-2-propen-1-one

【CA登记号】

【分子式】C₂₅H₂₇ClO₅

【分子量】442.93908

【元素组成】C 67.79% H 6.14% Cl 8% O 18.06%

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：(V)

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.

参考文献中间体

合成目标

【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