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【结 构 式】 
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【分子编号】59477 【品名】4-(2-propynyl)cyclohexanecarboxylic acid 【CA登记号】 |
【 分 子 式 】C10H14O2 【 分 子 量 】166.21996 【元素组成】C 72.26% H 8.49% O 19.25% |
合成路线1
该中间体在本合成路线中的序号：(XV)1,4-Cyclohexanedimethanol (X) was converted to the mono-tosylate (XI), which was then condensed with lithium acetylide ethylenediamine complex to furnish (4-propargylcyclohexyl)methanol (XII). This procedure was further improved with the protection of diol (X) as the mono-silyl ether (XIII). Tosylation of (XIII) and subsequent reaction with lithium acetylide afforded (XIV), which was then desilylated to (XII) by means of tetrabutylammonium fluoride. Alcohol (XII) was oxidized by Jones reagent to the corresponding carboxylic acid (XV). This was converted into the methyl ester (XVI) by treatment with trimethylsilyl diazomethane. Finally, palladium-catalyzed coupling of the iodopurine (IX) with acetylene (XVI) gave rise to the title compound.
| 【1】 Sullivan, G.W.; Rieger, J.M.; Brown, M.L.; Macdonald, T.L.; Linden, J.; Design, synthesis, and evaluation of novel A2A adenosine receptor agonists. J Med Chem 2001, 44, 4, 531. |
| 【2】 Linden, J.M.; MacDonald, T.; Glover, D.K.; Beller, G.A. (University of Virginia); Induction of pharmacological stress with adenosine receptor agonists. JP 2003502433; WO 0078774 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 22401 | (2S,3S,4R,5R)-5-(6-amino-2-iodo-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide | C12H15IN6O4 | 详情 | 详情 | |
| (X) | 59472 | [4-(hydroxymethyl)cyclohexyl]methanol | C8H16O2 | 详情 | 详情 | |
| (XI) | 59473 | [4-(hydroxymethyl)cyclohexyl]methyl 4-methylbenzenesulfonate | C15H22O4S | 详情 | 详情 | |
| (XII) | 59474 | [4-(2-propynyl)cyclohexyl]methanol | C10H16O | 详情 | 详情 | |
| (XIII) | 59475 | [4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclohexyl]methanol | C14H30O2Si | 详情 | 详情 | |
| (XIV) | 59476 | tert-butyl(dimethyl)silyl [4-(2-propynyl)cyclohexyl]methyl ether; tert-butyl(dimethyl){[4-(2-propynyl)cyclohexyl]methoxy}silane | C16H30OSi | 详情 | 详情 | |
| (XV) | 59477 | 4-(2-propynyl)cyclohexanecarboxylic acid | C10H14O2 | 详情 | 详情 | |
| (XVI) | 59478 | methyl 4-(2-propynyl)cyclohexanecarboxylate | C11H16O2 | 详情 | 详情 |