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【结 构 式】 
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【分子编号】33387 【品名】5-nitropentylamine; 5-nitro-1-pentanamine 【CA登记号】 |
【 分 子 式 】C5H12N2O2 【 分 子 量 】132.16256 【元素组成】C 45.44% H 9.15% N 21.2% O 24.21% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 1-amino-5-nitropentane (I) with benzyloxycarbonyl chloride (A) by means of NaOH in water gives 1-carbobenzoxyamino-5-nitropentane (II), which by reduction with Zn and ammonium chloride in ethanol - water yields 1-carbobenzoxyamino-5-hydroxylaminopentane (III). The reaction of (III) with succinic anhydride (B) by means of NaOH in pyridine water affords 1-carbobenzoxyamino-5-(N-succinylhydroxylamino)pentane (IV), which is cyclized with hot acetic anhydride giving 2-(5-carbobenzoxyaminopentyl)-3,6-dioxotetrahydro-1,2-oxazine (V). The reaction of (V) with the nitroamine (I) by means of sodium methoxide in methanol yields 1-carbobenzoxy-6-hydroxy-16-nitro-7,10-dioxo-6,11-diazahexadecane (VI), which is reduced with Zn and acetylated as before affording 1-carboxybenzoxyamino-6-hydroxy-16-(N-acetylhydroxylamino)-7,10-dioxo-6,11-diazahexadecane (VII).
| 【1】 Prelog, V.; Walser, A.; 75. Stoffweschselprodukte con actinomyceten. Uber die synthese der ferrioxamine B und D1. Helv Chim Acta 1962, 45, 631-637. |
| 【2】 Bickel, H.; et al.; 153. Stoffweschselprodukte von mikroorganismen. Zur henntnis von desferrioxamin B. Helv Chim Acta 1963, 46, 1385-89. |
| 【3】 Blancafort, P.; Castaner, J.; Serradell, M.N.; Hopkins, S.J.; Liposome-Entrapped Desferrioxamine deferoxamine. Drugs Fut 1979, 4, 7, 500. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 11291 | Dihydro-2,5-furandione; Succinic anhydride | 108-30-5 | C4H4O3 | 详情 | 详情 |
| (A) | 24261 | 1-[2-(chlorooxy)-2-oxoethyl]benzene | C8H7ClO2 | 详情 | 详情 | |
| (I) | 33387 | 5-nitropentylamine; 5-nitro-1-pentanamine | C5H12N2O2 | 详情 | 详情 | |
| (II) | 33388 | benzyl 5-nitropentylcarbamate | C13H18N2O4 | 详情 | 详情 | |
| (III) | 33389 | benzyl 5-(hydroxyamino)pentylcarbamate | C13H20N2O3 | 详情 | 详情 | |
| (IV) | 33390 | 4-[(5-[[(benzyloxy)carbonyl]amino]pentyl)(hydroxy)amino]-4-oxobutyric acid | C17H24N2O6 | 详情 | 详情 | |
| (V) | 33391 | benzyl 5-(3,6-dioxo-1,2-oxazinan-2-yl)pentylcarbamate | C17H22N2O5 | 详情 | 详情 | |
| (VI) | 33392 | benzyl 5-(hydroxy[4-[(5-nitropentyl)amino]-4-oxobutanoyl]amino)pentylcarbamate | C22H34N4O7 | 详情 | 详情 | |
| (VII) | 33393 | benzyl 5-[[4-([5-[acetyl(hydroxy)amino]pentyl]amino)-4-oxobutanoyl](hydroxy)amino]pentylcarbamate | C24H38N4O7 | 详情 | 详情 |