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【结 构 式】 
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【分子编号】56673 【品名】(Z)-1-(2-hydroxy-3-methoxyphenyl)-10-heptadecen-1-one 【CA登记号】 |
【 分 子 式 】C24H38O3 【 分 子 量 】374.56392 【元素组成】C 76.96% H 10.23% O 12.81% |
合成路线1
该中间体在本合成路线中的序号：(V)Irisquinone was originally isolated from some Iris species. The total synthesis of this compound has been reported by several procedures. 10-cis-Heptadecenoic acid (I) was converted to the Weinreb amide (II) via the corresponding acid chloride. Regiospecific ortho-lithiation of veratrole (III), followed by acylation with the N-methoxy amide (II), afforded ketone (IV). Selective mono-demethylation of (IV) with boron trichloride yielded phenol (V). Clemmensen reduction of the keto group of (V) employing zinc amalgam furnished 2-(cis-10-heptadecenyl)-6-methoxyphenol (VI). This was finally oxidized to the target quinone by means of oxygen gas in the presence of salcomine.
| 【1】 Haugwitz, R.D.; Risbood, P.A.; Parsons, J.L.; Myers, D.R.; Michalak, R.S.; Narayanan, V.L.; The synthesis of irisquinone. Tetrahedron Lett 1989, 30, 36, 4783. |
| 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) | 56670 | cis-10-Heptadecenoic acid | 29743-97-3 | C17H32O2 | 详情 | 详情 |
| (II) | 56671 | (Z)-N-methoxy-N-methyl-10-heptadecenamide | C19H37NO2 | 详情 | 详情 | |
| (III) | 17395 | 1-(4-fluorophenethyl)-4-piperidinecarboxamide | C14H19FN2O | 详情 | 详情 | |
| (IV) | 56672 | (Z)-1-(2,3-dimethoxyphenyl)-10-heptadecen-1-one | C25H40O3 | 详情 | 详情 | |
| (V) | 56673 | (Z)-1-(2-hydroxy-3-methoxyphenyl)-10-heptadecen-1-one | C24H38O3 | 详情 | 详情 | |
| (VI) | 56674 | 2-[(Z)-10-heptadecenyl]-6-methoxyphenol | C24H40O2 | 详情 | 详情 |