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【结 构 式】

【分子编号】23542

【品名】ethyl 3-oxo-4-phenoxybutanoate

【CA登记号】

【 分 子 式 】C12H14O4

【 分 子 量 】222.24076

【元素组成】C 64.85% H 6.35% O 28.8%

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)

The reaction of phenol (I) with ethyl 4-chloroacetoacetate (II) by means of KOH in DMSO gives ethyl 4 phenoxyacetoacetate (III), which by treatment with NH3 is converted into ethyl 3-amino-4-phenoxycrotonate (IV). The cyclization of (IV) with propargyl aldehyde (V) in hot toluene affords ethyl 2-(phenoxymethyl)nicotinate (VI), which is cyclized again by means of polyphosphoric acid (PPA) to yield 5,11-dihydro[1]benzoxepino[3,4-b)pyridin-5-one (VII). The reduction of (VII) with NaBH4 in ethanol gives the corresponding alcohol (VIII), which is finally condensed with N,N-diethylethylene diamine (IX) by means of SOCl2 in dichloromethane.

1 Harakawa, H.; Kumazawa, T.; Tanaka, H.; Oijo, Y.; Shuto, K.; Ishii, A.; Nakamizo, N.; Obase, H.; Oka, T.; Synthesis and antiulcer activity of 5,11-dihydro[1. J Med Chem 1988, 31, 4, 779.
2 Kumazawa, T.; Oiji, Y.; Shuto, K.; Tanaka, H. (Kyowa Hakko Kogyo Co., Ltd.); Benzepino[3,4-b]pyridine derivs.. EP 0129879; JP 1985006690; JP 1985078985; JP 1985089419; US 4547496 .
3 Castaner, J.; Prous, J.; KW-5805. Drugs Fut 1988, 13, 11, 954.
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) 23540 Phenol 108-95-2 C6H6O 详情 详情
(II) 23541 ethyl 4-chloro-3-oxobutanoate;Ethyl 4-chloro-3-oxobutanoate;Ethyl 4-chloroacetoacetate 638-07-3 C6H9ClO3 详情 详情
(III) 23542 ethyl 3-oxo-4-phenoxybutanoate C12H14O4 详情 详情
(IV) 23543 ethyl (Z)-3-amino-4-phenoxy-2-butenoate C12H15NO3 详情 详情
(V) 23544 propiolaldehyde C3H2O 详情 详情
(VI) 23545 ethyl 2-(phenoxymethyl)nicotinate C15H15NO3 详情 详情
(VII) 23546 [1]benzoxepino[3,4-b]pyridin-5(11H)-one C13H9NO2 详情 详情
(VIII) 23547 5,11-dihydro[1]benzoxepino[3,4-b]pyridin-5-ol C13H11NO2 详情 详情
(IX) 23548 N-(5,11-dihydro[1]benzoxepino[3,4-b]pyridin-5-yl)-N-[2-(dimethylamino)ethyl]amine; N(1)-(5,11-dihydro[1]benzoxepino[3,4-b]pyridin-5-yl)-N(2),N(2)-dimethyl-1,2-ethanediamine C17H21N3O 详情 详情
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