14-Acetoxy-3-tetradecyn-5-one | 159600-05-2

• 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: 14-Acetoxy-3-tetradecyn-5-one
• 英文别名: 10-oxotetradec-11-ynyl acetate
• CAS: 159600-05-2
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: LSWOMKWEDNEJHD-UHFFFAOYSA-N

物化性质

• 沸点：
  357.0±34.0 °C(predicted)
• 密度：
  0.963±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  14-Acetoxy-3-tetradecyn-5-one 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 30.0h， 以18.5%的产率得到10,10-Difluoro-11-tetradecynyl acetate
  参考文献：
  名称：

  Moth responses to selectively fluorinated sex pheromone analogs

  摘要：

  Partially fluorinated analogs of the European corn borer (Ostrinia nubilalis) female sex pheromone, 11-tetradecenyl acetate (97:3 Z: E), having mono- and trifluorosubstitutions at the terminal carbon of the pheromone chain, mimicked the biological activity of the pheromone, while analogs with fluorine at either side of the double bond and a pentafluoro analog were essentially inactive. Comparison of the pheromonal activity of these analogs with the previously reported activity of similarly fluorinated pheromones in five other species of moths revealed an unpredictable relationship between fluorine substitution pattern and pheromone-mimicking activity. Fluorine substitution pat terns that rendered pheromonal analogs biologically inactive in the European corn borer had no detrimental influence upon pheromonal activity in other species and the converse was also true. This is evidence that the relative importance of electronic qualities of sites within a pheromone molecule differ from species to species. Furthermore, it indicates that the biochemical components (pheromone receptor proteins, binding proteins, and enzymes) that make up moth olfactory chemosensory systems must also vary structurally from species to species, despite the fact that they are involved in olfactory sensing of compounds having very similar chemical structure.

  DOI：

  10.1007/bf02036202
• 作为产物：
  描述：

  10-(Tetrahydropyranyloxy)decanal 在 甲基锂 、 乙酰氯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 50.5h， 生成 14-Acetoxy-3-tetradecyn-5-one
  参考文献：
  名称：

  Moth responses to selectively fluorinated sex pheromone analogs

  摘要：

  Partially fluorinated analogs of the European corn borer (Ostrinia nubilalis) female sex pheromone, 11-tetradecenyl acetate (97:3 Z: E), having mono- and trifluorosubstitutions at the terminal carbon of the pheromone chain, mimicked the biological activity of the pheromone, while analogs with fluorine at either side of the double bond and a pentafluoro analog were essentially inactive. Comparison of the pheromonal activity of these analogs with the previously reported activity of similarly fluorinated pheromones in five other species of moths revealed an unpredictable relationship between fluorine substitution pattern and pheromone-mimicking activity. Fluorine substitution pat terns that rendered pheromonal analogs biologically inactive in the European corn borer had no detrimental influence upon pheromonal activity in other species and the converse was also true. This is evidence that the relative importance of electronic qualities of sites within a pheromone molecule differ from species to species. Furthermore, it indicates that the biochemical components (pheromone receptor proteins, binding proteins, and enzymes) that make up moth olfactory chemosensory systems must also vary structurally from species to species, despite the fact that they are involved in olfactory sensing of compounds having very similar chemical structure.

  DOI：

  10.1007/bf02036202