(E,E)-8,10-dodecadienyl trifluoromethyl ketone | 1185731-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,E)-8,10-dodecadienyl trifluoromethyl ketone
• 英文别名: E8E10-12:TFMK；(10E,12E)-1,1,1-trifluorotetradeca-10,12-dien-2-one
• CAS: 1185731-75-2
• 化学式: C₁₄H₂₁F₃O
• 分子量: 262.315
• InChiKey: SGHUJABGEZPODR-MQQKCMAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三氟乙酸乙酯 、 (E,E)-1-iodo-8,10-dodecadiene 在 叔丁基锂 、 水 、 氯化铵 作用下， 以 乙醚 、 正己烷 、 正戊烷 为溶剂， 反应 0.08h， 以81%的产率得到(E,E)-8,10-dodecadienyl trifluoromethyl ketone
  参考文献：
  名称：

  Development and Biological Activity of a New Antagonist of the Pheromone of the Codling Moth Cydia pomonella

  摘要：

  A new pheromone antagonist of the codling moth Cydia pomonella is reported. Presaturation of the antennae of the insects with vapors of the antagonist (E,E)-8,10-dodecadienyl trifluoromethyl ketone, analogue of the main component of the pheromone (codlemone), resulted in lower electrophysiological responses to the pheromone relative to untreated insects in the wind tunnel, the compound elicited a remarkable disruptive effect on all types of behavior of males flying toward a source baited with a pheromone antagonist blend in 11, 15, and 11 ratios. The insects displayed erratic flights in the presence of the antagonist, as shown by their flight parameters in comparison to insects attracted to the pheromone alone. In the field, traps baited with mixtures of 11 codlemone antagonist attracted considerably lower numbers of males than the natural attractant. The antagonist, however, did not inhibit the pheromone-degrading enzymes present in male antennae, suggesting that trifluoromethyl ketones are not sufficiently electrophilic to produce a stable intermediate adduct with a cysteine residue of the enzyme, a mechanism previously proposed for oxidase inhibition in insects. Overall and taking into account our previous reports and, of the pheromone of Sesamia nonagrioides (Sole,. ans, A. iho,. oSo,. Bosch,. P. Barrot, Palencia,. astelfii,. Guerrero. A. eduction of dama e by the Mediterrean corn borer, Sesamia nonagrioides, and the European corn borer, Ostrinia nubilalis, in maize fields by a trifluoromethyl ketone pheromone anologue. Entomol. Exp. Appl. 2008, 126, 28-39), the antagonist might be a ne candidate to consider in future strategies to control the codling moth.

  DOI：

  10.1021/jf901979k