(2Z,4E)-2-Bromo-hexa-2,4-dienenitrile | 910135-52-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (2Z,4E)-2-Bromo-hexa-2,4-dienenitrile
• CAS: 910135-52-3
• 化学式: C₆H₆BrN
• 分子量: 172.024
• InChiKey: XSPSIPQOHQUWFA-WIOWESQNSA-N

物化性质

• 沸点：
  214.8±23.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-2-Bromo-hexa-2,4-dienenitrile 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 异丙基溴化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (1E,3Z)-13-Hydroxy-cyclotrideca-1,3-dienecarbonitrile
  参考文献：
  名称：

  Studies towards the total synthesis of (−)-borrelidin: a strategy for the construction of the C11–C15 cyanodiene fragment and the utility of RCM for macrocyclization using model systems

  摘要：

  We report here a methodology for the construction of a conjugated cyanodiene synthon and the propensity of such synthons to participate in the olefin metathesis reaction. To this end, we have developed a strategy for the construction of the C11-C15 fragment of borrelidin and demonstrated the utility of the RCM reaction in the preparation of the final macrolide. To our knowledge, this is the first example of a RCM with a nitrile functionality on a diene. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.092
• 作为产物：
  描述：

  巴豆醛 、 α-Brom-α-cyano-methylen-triphenylphosphoran 以 二氯甲烷 为溶剂， 以58%的产率得到(2Z,4E)-2-Bromo-hexa-2,4-dienenitrile
  参考文献：
  名称：

  Studies towards the total synthesis of (−)-borrelidin: a strategy for the construction of the C11–C15 cyanodiene fragment and the utility of RCM for macrocyclization using model systems

  摘要：

  We report here a methodology for the construction of a conjugated cyanodiene synthon and the propensity of such synthons to participate in the olefin metathesis reaction. To this end, we have developed a strategy for the construction of the C11-C15 fragment of borrelidin and demonstrated the utility of the RCM reaction in the preparation of the final macrolide. To our knowledge, this is the first example of a RCM with a nitrile functionality on a diene. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.092