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【结 构 式】

【分子编号】65121

【品名】4-[4-(benzyloxy)benzyl]-4-hydroxy-3-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-yl pivalate

【CA登记号】

【 分 子 式 】C35H36O6

【 分 子 量 】552.66724

【元素组成】C 76.06% H 6.57% O 17.37%

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:(VII)

The title compound is synthesized starting from the natural isoflavone formononetin (I). Esterification of (I) with pivaloyl chloride (II) affords pivalate (III). Catalytic hydrogenation of (III) in the presence of Pd/BaSO4 leads to the chromane derivative (IV). The Grignard reagent (VI), prepared from 4-(benzyloxy)benzyl chloride (V), is then condensed with ketone (IV) to furnish the tertiary alcohol (VII). The O-benzyl protecting group of (VII) is then removed by catalytic hydrogenolysis to afford phenol (VIII). Alkylation of (VIII) with N-(2-chloroethyl)piperidine (IX) and K2CO3, with simultaneous pivalate ester hydrolysis, leads to the piperidylethyl ether (X). The tertiary alcohol of (X) is finally dehydrated by means of HCl in acetonitrile to provide the target compound (1,2).

1 Ghirardi, S.; Armani, E.; Amari, G.; Delcanale, M.; Civelli, M.; Caruso, P.; Galbiati, E.; Synthesis and pharmacological activity of CHF 4227, one of the most potent in vitro and in vivo SERMs till new discovered. Drugs Fut 2002, 27, Suppl. A.
2 Delcanale, M.; Civelli, M.; Armani, E.; Amari, G.; Galbiati, E. (Chiesi Farmaceutici SpA); 2H-1-Benzopyran derivs., processes for their preparation and pharmaceutical compsns. thereof. EP 1229036; EP 1281710; EP 1355906; WO 0259113 .
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) 65118 7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one C16H12O4 详情 详情
(II) 13597 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride 3282-30-2 C5H9ClO 详情 详情
(III) 65119 3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl pivalate C21H20O5 详情 详情
(IV) 65120 3-(4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl pivalate C21H22O5 详情 详情
(V) 65125 1-(benzyloxy)-4-(chloromethyl)benzene; benzyl 4-(chloromethyl)phenyl ether C14H13ClO 详情 详情
(VI) 65124 [4-(benzyloxy)benzyl](chloro)magnesium C14H13ClMgO 详情 详情
(VII) 65121 4-[4-(benzyloxy)benzyl]-4-hydroxy-3-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-yl pivalate C35H36O6 详情 详情
(VIII) 65122 4-hydroxy-4-(4-hydroxybenzyl)-3-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-yl pivalate C28H30O6 详情 详情
(IX) 10117 1-(2-Chloroethyl)piperidine; N-(2-Chloroethyl)piperidine 1932-03-2 C7H14ClN 详情 详情
(X) 65123 3-(4-methoxyphenyl)-4-{4-[2-(1-piperidinyl)ethoxy]benzyl}-4,7-chromanediol C30H35NO5 详情 详情
Extended Information