(7Z,13Z,16Z,19Z)-docosatetraenyl isobutyrate | 135459-81-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (7Z,13Z,16Z,19Z)-docosatetraenyl isobutyrate
• 英文别名: 7Z,13Z,16Z,19Z-Docosatetraenyl isobutyrate；[(7Z,13Z,16Z,19Z)-docosa-7,13,16,19-tetraenyl] 2-methylpropanoate
• CAS: 135459-81-3
• 化学式: C₂₆H₄₄O₂
• 分子量: 388.634
• InChiKey: IHFUWVNHVLVCKZ-LYBCEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  28
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (z,z,z,z)-7,13,16,19-Docosatetraen-1-ol 、 异丁酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (7Z,13Z,16Z,19Z)-docosatetraenyl isobutyrate
  参考文献：
  名称：

  Sex Pheromone of Browntail Moth, Euproctis chrysorrhea (L.): Synthesis and Field Deployment

  摘要：

  The browntail moth, Euproctis chrysorrhea (L.), is native to Eurasia, where periodic outbreaks result in defoliation of forest, shade, and ornamental trees. In addition to the damage caused by defoliation, human contact with larval urticating hairs often results in severe dermatitis. Hence, tools for monitoring and controlling the moth populations are desirable. The female-produced sex pheromone of the browntail moth was identified previously, but the synthesis had not been published. This paper reports the synthesis of the pheromone of the browntail moth, (7Z,13Z, 16Z,19Z)-docosatetraenyl isobutyrate, using in a key step a Wittig olefination of (62)-13-(tetrahydo-2H-pyran-2-yloxy)tridecenal. Field trapping studies were conducted with rubber septa and string formulations of the pheromone and included dose-response, pheromone purity, and dispenser-aging trials. It was found that traps baited with 250 mu g of pheromone of 91-94% isomeric purity (main impurity presumably being the 13E isomer) on rubber septa are suitable for monitoring moth populations during the entire flight season.

  DOI：

  10.1021/jf073161w