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【结 构 式】 
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【分子编号】52003 【品名】N(1)-(6-chloro-1-naphthyl)-1,2-ethanediamine; N-(2-aminoethyl)-N-(6-chloro-1-naphthyl)amine 【CA登记号】 |
【 分 子 式 】C12H13ClN2 【 分 子 量 】220.7014 【元素组成】C 65.31% H 5.94% Cl 16.06% N 12.69% |
合成路线1
该中间体在本合成路线中的序号：(V)The peroxidation of 1,4-diphenyl-1-cyclopentadiene (I) with O2, white light and activated by tetraphenylporphyrin in dichloromethane gives the peroxide (II), which is condensed with cyclohexane-1,4-dione (III) by means of trimethylsilyl trifluoromethanesulfonate in dichloromethane, yielding the adduct (IV). The reductocondensation of (IV) with N-(7-chloroquinolin-4-yl)ethylenediamine (V) by means of NaBH(OAc)3 in dichloromethane affords the tricyclic trioxane (VI), which is finally treated with citric acid in acetone to provide the target citrate. The intermediate N-(7-chloroquinolin-4-yl)ethylenediamine (V) has been obtained by reaction of 4,7-dichloroquinoline (VIII) with ethylenediamine by means of NaOH at 85 C.
| 【1】 Dechy-Cabaret, O.; et al.; Preparation of antimalarial activities of "trioxaquines", new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline. ChemBioChem 2000, 1, 4, 281. |
| 【2】 Robert, A.; Dechy Cabaret, O.; Meunier, B.; Benoit Vical, F. (CNRS (Centre National de la Recherche Scientifique)); Dual molecules containing a peroxide deriv., synthesis and therapeutic applications thereof. FR 2807433; WO 0177105 . |
| 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) | 51999 | 1-(4-phenyl-1,3-cyclopentadien-1-yl)benzene | C17H14 | 详情 | 详情 | |
| (II) | 52000 | 1,4-diphenyl-2,3-dioxabicyclo[2.2.1]hept-5-ene | C17H14O2 | 详情 | 详情 | |
| (III) | 52001 | 1,4-Cyclohexanedione; Tetrahydro-p-benzoquinone | 637-88-7 | C6H8O2 | 详情 | 详情 |
| (IV) | 52002 | C23H22O4 | 详情 | 详情 | ||
| (V) | 52003 | N(1)-(6-chloro-1-naphthyl)-1,2-ethanediamine; N-(2-aminoethyl)-N-(6-chloro-1-naphthyl)amine | C12H13ClN2 | 详情 | 详情 | |
| (VI) | 52004 | C35H35ClN2O3 | 详情 | 详情 | ||
| (VII) | 13856 | 2-Hydroxy-1,2,3-propanetricarboxylic acid; Citric acid | 77-92-9 | C6H8O7 | 详情 | 详情 |
| (VIII) | 52005 | 1,6-dichloronaphthalene | C10H6Cl2 | 详情 | 详情 | |
| (IX) | 14754 | ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine | 107-15-3 | C2H8N2 | 详情 | 详情 |