• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】18886

【品名】1-(6-amino-1,3-benzodioxol-5-yl)-1-ethanone

【CA登记号】28657-75-2

【 分 子 式 】C9H9NO3

【 分 子 量 】179.1754

【元素组成】C 60.33% H 5.06% N 7.82% O 26.79%

与该中间体有关的原料药合成路线共 3 条

合成路线1

该中间体在本合成路线中的序号:(I)

The compound was prepared by condensation of acetophenone (I) with 3-flourobenzaldehyde (II) in refluxing ethanolic NaOH, followed by cyclization of the intermediate chalcone in diphenyl ether at 180 C.

1 Xia, Y.; et al.; Antitumor agents. 181. Synthesis and biological evaluation of 6,7,2',3',4'-substituted-1,2,3, 4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents. J Med Chem 1998, 41, 7, 1155.
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) 18886 1-(6-amino-1,3-benzodioxol-5-yl)-1-ethanone 28657-75-2 C9H9NO3 详情 详情
(II) 18887 3-Fluorobenzaldehyde 456-48-4 C7H5FO 详情 详情
(III) 18888 (E)-1-(6-amino-1,3-benzodioxol-5-yl)-3-(3-fluorophenyl)-2-propen-1-one C16H12FNO3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

The reduction of 2-nitro-4,5-methylenedioxyacetophenone (I) with H2 over PtO2 in ethanol gives 2-amino-4,5-methylenedioxyacetophenone (II), which is cyclized by treatment with NaNO2 and HCl in water yielding 6,7-methylenedioxycinnolin-4-ol (III). The bromination of (III) with Br2 and potassium acetate in refluxing acetic acid affords 3-bromo-6,7-methylenedioxycinnolin-4-ol (IV), which is treated with Cu2(CN)2 in refluxing DMF giving 4-hydroxy-6,7-methylenedioxycinnolin-3-carbonitrile (V). Alkylation of (V) with ethyl iodide (A) by means of NaH in DMF affords 1-ethyl-6,7-methylenedioxy-4(1H)-oxocinnolin-3-carbonitrile (VI), which is finally hydrolyzed with HCl in refluxing acetic acid.

1 Roberts, P.J.; Castañer, J.; Cinoxacin. Drugs Fut 1978, 3, 1, 22.
2 Un metodo para la preparacion de acidos 6,7-metilendioxi-4(1H)-oxocinnolin-3-carboxilicos. ES 376173; ES 402312 .
3 Maas, I.M. Pfeiffer, W.G.; Voithenleitner, F.; 1-niederalkyl- oder -alkylensubstituierte 6,7-Methylendioxyd-4(1H)-oxocinnolin-3-carbosauren und Zwiswhenprodukte dafur. DE 2005104; FR 2034519; GB 1296753; GB 1296754 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 10925 Iodoethane;ethyl iod 75-03-6 C2H5I 详情 详情
(I) 39691 1-(6-nitro-1,3-benzodioxol-5-yl)-1-ethanone 56136-84-6 C9H7NO5 详情 详情
(II) 18886 1-(6-amino-1,3-benzodioxol-5-yl)-1-ethanone 28657-75-2 C9H9NO3 详情 详情
(III) 39692 [1,3]dioxolo[4,5-g]cinnolin-4-ol C9H6N2O3 详情 详情
(IV) 39693 3-bromo[1,3]dioxolo[4,5-g]cinnolin-4-ol C9H5BrN2O3 详情 详情
(V) 39694 4-hydroxy[1,3]dioxolo[4,5-g]cinnoline-3-carbonitrile C10H5N3O3 详情 详情
(VI) 39695 1-ethyl-4-oxo-1,4-dihydro[1,3]dioxolo[4,5-g]cinnoline-3-carbonitrile C12H9N3O3 详情 详情

合成路线3

该中间体在本合成路线中的序号:(I)

The desired 2'-amino chalcone is synthesized by a base-catalyzed condensation of 2-amino acetophenone (I) and benzaldehyde (II) by means of aqueous NaOH in EtOH.

1 Xia, Y.; et al.; Antitumor agents. 181. Synthesis and biological evaluation of 6,7,2',3',4'-substituted-1,2,3, 4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents. J Med Chem 1998, 41, 7, 1155.
2 Xia, P.; Xia, Y.; Lee, K.-H.; Bastow, K.F.; Nakanishi, Y.; Yang, Z.-Y.; Antitumor agents. Part 202: Novel 2'-amino chalcones: Design, synthesis and biological evaluation. Bioorg Med Chem Lett 2000, 10, 8, 699.
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) 18886 1-(6-amino-1,3-benzodioxol-5-yl)-1-ethanone 28657-75-2 C9H9NO3 详情 详情
(II) 20589 3-methoxybenzaldehyde; m-Anisaldehyde 591-31-1 C8H8O2 详情 详情
Extended Information