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【结 构 式】 
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【分子编号】48514 【品名】(1R,2R)-N(1)-(2-[[(1R,2R)-2-aminocyclohexyl]amino]ethyl)-1,2-cyclohexanediamine; N-[(1R,2R)-2-aminocyclohexyl]-N-(2-[[(1R,2R)-2-aminocyclohexyl]amino]ethyl)amine 【CA登记号】 |
【 分 子 式 】C14H30N4 【 分 子 量 】254.41916 【元素组成】C 66.09% H 11.89% N 22.02% |
合成路线1
该中间体在本合成路线中的序号：(VI)Treatment of (R,R)-1,2-diaminocyclohexane (I) with triphenylmethyl chloride produced the N-trityl derivative (II). Subsequent condensation of (II) with glyoxal (III) gave the bis-imine (IV), which was reduced to amine (V) using LiBH4. Cleavage of the N-trityl groups of (V) with HCl in acetone afforded tetraamine (VI). This was then condensed with 2,6-diacetylpyridine (VII) in the presence of MnCl2 to furnish the cyclic bis-imine manganese complex (VIII). Finally, transfer hydrogenation of the imine functions of (VIII) using ammonium formate and Pd/C produced the cyclic pentaamino derivative as a diastereomeric mixture. The title isomer was then purified by separative partition between H2O and CH2Cl2.
| 【1】 Udipi, K.; Joardar, S.; Forster, D.; Riley, D.; Henke, S.; Brethaur, K.; Thurmond, B.; Ornberg, R. (Pharmacia Corp.); Biomaterials modified with superoxide dismutase mimics. WO 0072893 . |
| 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) | 11130 | (1R,2R)-1,2-cyclohexanediamine; (1R,2R)-2-aminocyclohexylamine; cis-1,2-Diaminocyclohexane | 20439-47-8 | C6H14N2 | 详情 | 详情 |
| (II) | 48511 | N-[(1R,2R)-2-aminocyclohexyl]-N-tritylamine; (1R,2R)-N(1)-trityl-1,2-cyclohexanediamine | C25H28N2 | 详情 | 详情 | |
| (III) | 32557 | glyoxal; 2-oxoacetaldehyde | 107-22-2 | C2H2O2 | 详情 | 详情 |
| (IV) | 48512 | (1R,2R)-N(1)-trityl-N(2)-((E)-2-[[(1R,2R)-2-(tritylamino)cyclohexyl]imino]ethylidene)-1,2-cyclohexanediamine; N-trityl-N-[(1R,2R)-2-[((E)-2-[[(1R,2R)-2-(tritylamino)cyclohexyl]imino]ethylidene)amino]cyclohexyl]amine | C52H54N4 | 详情 | 详情 | |
| (V) | 48513 | (1R,2R)-N(1)-trityl-N(2)-(2-[[(1R,2R)-2-(tritylamino)cyclohexyl]amino]ethyl)-1,2-cyclohexanediamine; N-trityl-N-[(1R,2R)-2-[(2-[[(1R,2R)-2-(tritylamino)cyclohexyl]amino]ethyl)amino]cyclohexyl]amine | C52H58N4 | 详情 | 详情 | |
| (VI) | 48514 | (1R,2R)-N(1)-(2-[[(1R,2R)-2-aminocyclohexyl]amino]ethyl)-1,2-cyclohexanediamine; N-[(1R,2R)-2-aminocyclohexyl]-N-(2-[[(1R,2R)-2-aminocyclohexyl]amino]ethyl)amine | C14H30N4 | 详情 | 详情 | |
| (VII) | 48515 | 2,6-Diacetylpyridine | 1129-30-2 | C9H9NO2 | 详情 | 详情 |
| (VIII) | 48516 | (4R,9R,14R,19R)-2,21-dimethyl-3,10,13,20,26-pentaazatetracyclo[20.3.1.0(4,9).0(14,19)]hexacosa-1(26),2,20,22,24-pentaene | C23H35N5 | 详情 | 详情 |