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【结 构 式】 
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【分子编号】59093 【品名】5-dodecynenitrile 【CA登记号】 |
【 分 子 式 】C12H19N 【 分 子 量 】177.2896 【元素组成】C 81.3% H 10.8% N 7.9% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(XXVII)The precursor cis-dodec-5-enoic acid (XXIX) was prepared as shown in Scheme 4. The lithium acetylide of 1-octyne (XXIV) was alkylated with 1,3-diiodopropane (XXV) to give the iodoalkyne (XXVI). Displacement of the iodide of (XXVI) with KCN in hot DMSO provided nitrile (XXVII), which was hydrolyzed to the corresponding carboxylic acid (XXVIII) employing KOH in ethylene glycol at 140 C. Partial hydrogenation of the triple bond in the presence of poisoned Lindlar catalyst furnished the (Z)-olefin (XXIX).
| 【1】 Christ, W.J.; Kawata, T.; Hawkins, L.D.; Kobayashi, S.; Asano, O.; Rossignol, D.P. (Eisai Co., Ltd.); Anti-endotoxin cpds.. EP 0536969; JP 1993194470; US 5530113 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXIV) | 59091 | 1-octyne | C8H14 | 详情 | 详情 | |
| (XXV) | 42364 | 1,3-diiodopropane | 627-31-6 | C3H6I2 | 详情 | 详情 |
| (XXVI) | 59092 | 1-iodo-4-undecyne | C11H19I | 详情 | 详情 | |
| (XXVII) | 59093 | 5-dodecynenitrile | C12H19N | 详情 | 详情 | |
| (XXVIII) | 59094 | 5-dodecynoic acid | C12H20O2 | 详情 | 详情 | |
| (XXIX) | 49124 | (Z)-5-dodecenoic acid | C12H22O2 | 详情 | 详情 |
Extended Information