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【结 构 式】 
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【分子编号】48955 【品名】1-[(4-methyl-1-pentynyl)oxy]cyclohexane; cyclohexyl 4-methyl-1-pentynyl ether 【CA登记号】 |
【 分 子 式 】C12H20O 【 分 子 量 】180.2902 【元素组成】C 79.94% H 11.18% O 8.87% |
合成路线1
该中间体在本合成路线中的序号：(XXIII)Synthesis of the intermediate vinyl cuprate (XXV): The reaction of cyclohexyloxyacetylene (XXI) with iso-butyl triflate (XXII) by means of BuLi gives the adduct (XXIII), which is brominated with Tms-Br, yielding the vinyl bromide (XXIV). Finally, this compound is treated with CuCN, LiCl and tBuLi in THF to afford the desired vinyl cuprate intermediate (XXV).
| 【1】 Jin, Z.; Yu, W.; A new strategy for the stereoselective introduction of steroid side chain via alpha-alkoxy vinyl cuprates: Total synthesis of a highly potent antitumor natural product OSW-1. J Am Chem Soc 2001, 123, 14, 3369. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXI) | 48953 | 1-(ethynyloxy)cyclohexane; cyclohexyl ethynyl ether | C8H12O | 详情 | 详情 | |
| (XXII) | 48954 | isobutyl trifluoromethanesulfonate | C5H9F3O3S | 详情 | 详情 | |
| (XXIII) | 48955 | 1-[(4-methyl-1-pentynyl)oxy]cyclohexane; cyclohexyl 4-methyl-1-pentynyl ether | C12H20O | 详情 | 详情 | |
| (XXIV) | 48956 | (E)-1-bromo-4-methyl-1-pentenyl cyclohexyl ether; 1-[[(E)-1-bromo-4-methyl-1-pentenyl]oxy]cyclohexane | C12H21BrO | 详情 | 详情 | |
| (XXV) | 48957 | C54H99CuNO4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XXIII)Alpha-(cyclohexloxy)vinyl bromide (XXIV): The reaction of (cyclohexyloxy)acetylene (XXI) with isobutyl triflate (XXII) by means of BuLi gives 1-(cyclohexyloxy)-4-methyl-1-pentyne (XXIII), which is then brominated to the target vinyl bromide (XXIV) by means of Tms-Br in methanol
| 【1】 Yu, W.; Jin, Z.; Total synthesis of the anticancer natural product OSW-1. J Am Chem Soc 2002, 124, 23, 6576. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXI) | 48953 | 1-(ethynyloxy)cyclohexane; cyclohexyl ethynyl ether | C8H12O | 详情 | 详情 | |
| (XXII) | 48954 | isobutyl trifluoromethanesulfonate | C5H9F3O3S | 详情 | 详情 | |
| (XXIII) | 48955 | 1-[(4-methyl-1-pentynyl)oxy]cyclohexane; cyclohexyl 4-methyl-1-pentynyl ether | C12H20O | 详情 | 详情 | |
| (XXIV) | 48956 | (E)-1-bromo-4-methyl-1-pentenyl cyclohexyl ether; 1-[[(E)-1-bromo-4-methyl-1-pentenyl]oxy]cyclohexane | C12H21BrO | 详情 | 详情 |