(Z)-1-bromo-1-hepten-4-yne | 706820-70-4

• 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: (Z)-1-bromo-1-hepten-4-yne
• 英文别名: (Z)-1-bromohept-1-en-4-yne
• CAS: 706820-70-4
• 化学式: C₇H₉Br
• 分子量: 173.052
• InChiKey: IROYCJRAPRRDMI-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  0.43
• 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：

  (Z)-1-bromo-1-hepten-4-yne 在 P₂-Ni 氢气 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 rac-(cis)-(2Z,5Z-octadienyl)-3-nonyloxirane
  参考文献：
  名称：

  Improved Synthesis and Deployment of (2S,3R)-2-(2Z,5Z-Octadienyl)-3-nonyloxirane, a Pheromone of the Pink Moth, Lymantria mathura

  摘要：

  We report two new syntheses of (2S,3R)-2-(2Z5Z-octadienyl)-3-nonyloxirane, the main sex pheromone component of the pink moth, Lymantria mathura. The key step in the first route was the construction of (Z,Z)-1-bromo-1,4-heptadiene (6), which was coupled in the final step with 2-iodomethyl-3-nonyloxirane 4 via a Grignard reaction. The second approach employed alkylation of 1,4-heptadiynyllithium with epoxy triflates 7 in ether/hexane and provided the pheromone in greater than or equal to37% overall yield from alcohol 2. The 4:1 ratio of pheromone enantiomers, reportedly the most attractive to pink moth males, can be directly crafted from appropriately selected Sharpless asymmetric epoxidation conditions.

  DOI：

  10.1021/jf035506q
• 作为产物：
  描述：

  1-丁炔 、 1,3-二溴-1-丙烯 在 乙基溴化镁 、 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醚 、 六甲基磷酰三胺 为溶剂， 生成 (Z)-1-bromo-1-hepten-4-yne
  参考文献：
  名称：

  Improved Synthesis and Deployment of (2S,3R)-2-(2Z,5Z-Octadienyl)-3-nonyloxirane, a Pheromone of the Pink Moth, Lymantria mathura

  摘要：

  We report two new syntheses of (2S,3R)-2-(2Z5Z-octadienyl)-3-nonyloxirane, the main sex pheromone component of the pink moth, Lymantria mathura. The key step in the first route was the construction of (Z,Z)-1-bromo-1,4-heptadiene (6), which was coupled in the final step with 2-iodomethyl-3-nonyloxirane 4 via a Grignard reaction. The second approach employed alkylation of 1,4-heptadiynyllithium with epoxy triflates 7 in ether/hexane and provided the pheromone in greater than or equal to37% overall yield from alcohol 2. The 4:1 ratio of pheromone enantiomers, reportedly the most attractive to pink moth males, can be directly crafted from appropriately selected Sharpless asymmetric epoxidation conditions.

  DOI：

  10.1021/jf035506q