(2Z,5E)-1-bromo-octa-2,5-diene | 292821-76-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (2Z,5E)-1-bromo-octa-2,5-diene
• CAS: 292821-76-2
• 化学式: C₈H₁₃Br
• 分子量: 189.095
• InChiKey: JQVHFVXDXITBCJ-FDTUMDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  9.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  9-(2-tetrahydropyranyloxy)-1-nonyne 、 (2Z,5E)-1-bromo-octa-2,5-diene 在 甲基氯化镁 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 2-((E)-10-vinyl-pentadec-12-en-8-ynyloxy)-tetrahydro-pyran 、 2-((11Z,14E)-heptadeca-11,14-dien-8-ynyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  Large-scale preparation of (9Z,12E)-[1-13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1-13C]-octadeca-9,12,15-trienoic acid and their [1-13C] all-cis isomers

  摘要：

  Several grams of labelled trans linoleic and linolenic acids with high chemical and isomeric purities (> 97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1-C-13]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1-C-13]-octadeca-9,12,15-trienoic acid were obtained in, respectively: seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-C-13]-octadeca-9,12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-C-13]-octadeca-9,12,15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities ( > 0.5%) of each labelled fatty acid have been characterised. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(00)00137-7
• 作为产物：
  描述：

  (E)-oct-5-en-2-yn-1-ol 在 Lindlar's catalyst 吡啶 、 喹啉 、 氢气 、 三溴化磷 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 4.0h， 生成 (2Z,5E)-1-bromo-octa-2,5-diene
  参考文献：
  名称：

  Large-scale preparation of (9Z,12E)-[1-13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1-13C]-octadeca-9,12,15-trienoic acid and their [1-13C] all-cis isomers

  摘要：

  Several grams of labelled trans linoleic and linolenic acids with high chemical and isomeric purities (> 97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1-C-13]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1-C-13]-octadeca-9,12,15-trienoic acid were obtained in, respectively: seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-C-13]-octadeca-9,12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-C-13]-octadeca-9,12,15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities ( > 0.5%) of each labelled fatty acid have been characterised. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(00)00137-7