(6Z)-13-(tetrahydro-2H-pyran-2-yloxy)tridecenal | 1009088-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (6Z)-13-(tetrahydro-2H-pyran-2-yloxy)tridecenal
• 英文别名: (Z)-13-(oxan-2-yloxy)tridec-6-enal
• CAS: 1009088-37-2
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: LVTIAYWPUJBLRG-UPHRSURJSA-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：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6Z)-13-(tetrahydro-2H-pyran-2-yloxy)tridecenal 、 (Z,Z)-3,6-Nonadienyltriphenylphosphonium tosylate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以680 mg的产率得到2-[(7Z,13Z,16Z,19Z)-docosa-7,13,16,19-tetraenoxy]oxane
  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：

  (6Z)-13-(tetrahydro-2H-pyran-2-yloxy)tridecen-1-ol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到(6Z)-13-(tetrahydro-2H-pyran-2-yloxy)tridecenal
  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.