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【结 构 式】 
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【分子编号】25854 【品名】ethyl 4-(4-[4-[ethoxy(imino)methyl]phenyl]-2-furyl)benzenecarboximidoate 【CA登记号】 |
【 分 子 式 】C22H22N2O3 【 分 子 量 】362.42836 【元素组成】C 72.91% H 6.12% N 7.73% O 13.24% |
合成路线1
该中间体在本合成路线中的序号：(VII)Aldol condensation of 4-cyanobenzaldehyde (II) with 4-cyano-acetophenone (I) in methanolic NaOH furnished chalcone (III). Subsequent addition of bromine to (III) gave dibromide (IV). This was treated with NaOMe to produce the intermediate enol ether (V), which was then condensed with the ylide generated from trimethylsulfonium iodide and NaH to afford the 2,4-diarylfuran (VI). Acid-catalyzed addition of EtOH to (VI) provided the corresponding bis(imidate) (VII). Further reaction of (VII) with isopropylamine yielded the target amidine, which was isolated as the dihydrochloride salt.
| 【1】 Francesconi, I.; et al.; 2,4-Diphenyl furan diamidines as novel anti-pneumocystis carinii pneumonia agents. J Med Chem 1999, 42, 12, 2260. |
| 【2】 Boykin, D.W.; Francesconi, I.; Tidwell, R.R.; Wilson, D.W. (Georgia State University; University of North Carolina); 2,4-Bis (4-amidino)phenyl furans as anti-Pneumocystis carinii agents. EP 0941991; GB 2334716; US 6008247 . |
| 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) | 25849 | 4-acetylbenzonitrile | 1443-80-7 | C9H7NO | 详情 | 详情 |
| (II) | 17552 | 4-formylbenzonitrile; 4-Cyanobenzaldehyde | 105-07-7 | C8H5NO | 详情 | 详情 |
| (III) | 25580 | 3-amino-2-methylpropanenitrile | C4H8N2 | 详情 | 详情 | |
| (IV) | 25851 | 4-[2,3-dibromo-3-(4-cyanophenyl)propanoyl]benzonitrile | C17H10Br2N2O | 详情 | 详情 | |
| (V) | 25852 | 4-[(Z)-3-(4-cyanophenyl)-3-methoxy-2-propenoyl]benzonitrile | C18H12N2O2 | 详情 | 详情 | |
| (VI) | 25853 | 4-[4-(4-cyanophenyl)-2-furyl]benzonitrile | C18H10N2O | 详情 | 详情 | |
| (VII) | 25854 | ethyl 4-(4-[4-[ethoxy(imino)methyl]phenyl]-2-furyl)benzenecarboximidoate | C22H22N2O3 | 详情 | 详情 |