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【结 构 式】 
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【分子编号】54787 【品名】(1R,4S,5R,8S,9R,10R,12R,13R)-10-allyl-1,5,9,12-tetramethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadecane 【CA登记号】 |
【 分 子 式 】C19H30O4 【 分 子 量 】322.4448 【元素组成】C 70.77% H 9.38% O 19.85% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of dihydroartemisinin (I) with benzoyl chloride in pyridine gives the benzoate (II), which is treated with alyltrimethylsilane (III) and ZnCl2 in dichloroethane to yield the allyl-artemisinin derivative (IV). The ozonolysis of the vinyl group of (IV), followed by reduction with NaBH4, affords the 2-hydroxyethyl derivative (V). The reaction of (V) with Ms-Cl and TEA provides the mesylate (VI), which is finally condensed with 1-[3-(trifluoromethyl)phenyl]piperazine (VII) in refluxing benzene to furnish the target piperazinylethyl derivative.
| 【1】 Hindley, S.; Bray, P.G.; Ward, S.A.; Searle, N.L.; Park, B.K.; Davies, J.; O'Neill, P.M.; Storr, R.C.; Mechanism-based design of parasite-targeted artemisinin derivatives: Synthesis and antimalarial activity of new diamine containing analogues. J Med Chem 2002, 45, 5, 1052. |
| 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) | 54785 | (1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9,12-tetramethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadecan-10-ol | C16H26O5 | 详情 | 详情 | |
| (II) | 54786 | (1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9,12-tetramethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl benzoate | C23H30O6 | 详情 | 详情 | |
| (III) | 15775 | Allyltrimethylsilane; allyl(trimethyl)silane | 762-72-1 | C6H14Si | 详情 | 详情 |
| (IV) | 54787 | (1R,4S,5R,8S,9R,10R,12R,13R)-10-allyl-1,5,9,12-tetramethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadecane | C19H30O4 | 详情 | 详情 | |
| (V) | 54788 | 2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9,12-tetramethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]-1-ethanol | C18H30O5 | 详情 | 详情 | |
| (VI) | 54789 | 2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9,12-tetramethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]ethyl methanesulfonate | C19H32O7S | 详情 | 详情 | |
| (VII) | 16172 | 1-[3-(trifluoromethyl)phenyl]piperazine; N-[3-(trifluoromethyl)phenyl]piperazine | 15532-75-9 | C11H13F3N2 | 详情 | 详情 |