rac-(cis)-2-(2,5-octadiynyl)-3-nonyloxirane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: rac-(cis)-2-(2,5-octadiynyl)-3-nonyloxirane
• 英文别名: (2S,3R)-2-nonyl-3-octa-2,5-diynyloxirane
• 化学式: C₁₉H₃₀O
• 分子量: 274.447
• InChiKey: RVOHNZFQOYRPNL-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  rac-(cis)-2-(2,5-octadiynyl)-3-nonyloxirane 在 Lindlar's catalyst 喹啉 、 氢气 、 环己烯 作用下， 以 甲醇 为溶剂， 反应 1.0h， 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：

  (±)-(3-nonyloxiran-2-yl)methanol 在 2,6-二甲基吡啶 、 正丁基锂 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 rac-(cis)-2-(2,5-octadiynyl)-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

文献信息

• Improved Synthesis and Deployment of (2<i>S</i>,3<i>R</i>)-2-(2<i>Z</i>,5<i>Z</i>-Octadienyl)-3-nonyloxirane, a Pheromone of the Pink Moth, <i>Lymantria mathura</i>
  作者：Ashot Khrimian、James E. Oliver、Roger C. Hahn、Nikki H. Dees、Jeff White、Victor C. Mastro

  DOI：10.1021/jf035506q

  日期：2004.5.1

  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.