13-(四氢-2H-吡喃-2-氧基)-6-十三碳炔-1-醇 | 1009088-35-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 13-(四氢-2H-吡喃-2-氧基)-6-十三碳炔-1-醇
• 英文名称: 13-(tetrahydro-2H-pyran-2-yloxy)-6-tridecyn-1-ol
• 英文别名: 13-(Oxan-2-yloxy)tridec-6-yn-1-ol
• CAS: 1009088-35-0
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: BEUDYRDVTTWJLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  13-(四氢-2H-吡喃-2-氧基)-6-十三碳炔-1-醇 在 5% Pd-CaCO3 、 氢气 作用下， 以 正己烷 为溶剂， 反应 4.0h， 以1.16 g的产率得到(6Z)-13-(tetrahydro-2H-pyran-2-yloxy)tridecen-1-ol
  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
• 作为产物：
  描述：

  2-(6-溴己氧基)四氢吡喃 、 6-庚炔醇 在 甲基锂 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 以67%的产率得到13-(四氢-2H-吡喃-2-氧基)-6-十三碳炔-1-醇
  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

文献信息

• Sex Pheromone of Browntail Moth, Euproctis chrysorrhea (L.): Synthesis and Field Deployment
  作者：Ashot Khrimian、David R. Lance、Meier Schwarz、Barbara A. Leonhardt、Victor C. Mastro

  DOI：10.1021/jf073161w

  日期：2008.4.1

  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.