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【结 构 式】 
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【分子编号】43378 【品名】3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propanamide 【CA登记号】 |
【 分 子 式 】C17H27NO2 【 分 子 量 】277.40692 【元素组成】C 73.61% H 9.81% N 5.05% O 11.53% |
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：(IV)Catalytic hydrogenation of 3,5-di-tert-butyl-4-hydroxycinnamic acid (I) afforded the saturated carboxylic acid (II), which was converted into amide (IV) via the corresponding acid chloride (III). Reduction of the amide function of (IV) by means of LiAlH4 furnished the primary amine (V). This was condensed with O-benzyl maltol (VI) to produce the pyridone (VII). After hydrogenolysis of the benzyl protecting group of (VII), the title compound was isolated as the corresponding mesylate salt.
| 【1】 Malcolm, C.S.; Bebbington, D.; Monck, N.J.T.; Palmer, A.M.; Gaur, S.; Benwell, K.; Porter, R.H.P.; Harvey, V.; 3,5-Disubstituted-4-hydroxyphenyls linked to 3-hydroxy-2-methyl-4(1H)-pyridinone: Potent inhibitors of lipid peroxidation and cell toxicity. J Med Chem 2000, 43, 15, 2779. |
| 【2】 Malcolm, C.; Porter, R.; Bebbington, D.; Palmer, A.; Gaur, S.; Monck, N. (Vernalis Research Ltd.); Ortho-hydroxypyridinone derivs. as iron chelating and antioxidant agents. EP 1027335; WO 9923075 . |
| 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) | 43375 | (E)-3-[3,5-di(tert-butyl)-4-hydroxyphenyl]-2-propenoic acid | 22014-01-3 | C17H24O3 | 详情 | 详情 |
| (II) | 43376 | 3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propionic acid | 20170-32-5 | C17H26O3 | 详情 | 详情 |
| (III) | 43777 | 5,5,8,8-tetramethyl-N-(2-nitrophenyl)-5,6,7,8-tetrahydro-2-naphthalenamine; N-(2-nitrophenyl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)amine | C20H24N2O2 | 详情 | 详情 | |
| (IV) | 43378 | 3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propanamide | C17H27NO2 | 详情 | 详情 | |
| (V) | 43379 | 4-(3-aminopropyl)-2,6-di(tert-butyl)phenol | C17H29NO | 详情 | 详情 | |
| (VI) | 12074 | 3-(Benzyloxy)-2-methyl-4H-pyran-4-one；3-(benzyloxy)-2-methylpyran-4-one | 61049-69-2 | C13H12O3 | 详情 | 详情 |
| (VII) | 43380 | 3-(benzyloxy)-1-[3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propyl]-2-methyl-4(1H)-pyridinone | C30H39NO3 | 详情 | 详情 |
Extended Information