(2E,4E)-2-Ethyl-4-methyl-hexa-2,4-dienoic acid ethyl ester | 221338-36-9

• 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: (2E,4E)-2-Ethyl-4-methyl-hexa-2,4-dienoic acid ethyl ester
• CAS: 221338-36-9
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: ZUEQWFRMWDMYTG-MUDDOMJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2E,4E)-2-Ethyl-4-methyl-hexa-2,4-dienoic acid ethyl ester 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 生成 (1E,3E,5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene
  参考文献：
  名称：

  Reduction of Carpophilus freemani Dobson (Coleoptera:  Nitidulidae) Aggregation Pheromone Response by Synthetic Analogues

  摘要：

  Analogues of (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene the major component of the aggregation pheromone of Carpophilus freemani Dobson (Coleoptera: Nitidulidae), were synthesized and the potency of these compounds in suppressing the response of C. freemani to its pheromone in a wind tunnel bioassay was determined. The most potent compounds reduced behavioral response to pheromone 83-96% when the inhibitors were present in 10-fold excess. These compounds are (1Z,3E,5E)-1-methoxy-3-ethyl-5-methyl-1,3,5-heptatriene, (1E,3E,5E)- 1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene, and (1Z,3E,5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene. In the presence of fermenting bread dough (a pheromone synergist), the most potent inhibitory compound, (IZ,3E,5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene, was less effective in reducing mean landings (69% vs 99%) than when dough was absent. This inhibitory compound causes a reduction of response to pheromone but does not cause a reduction of response to fermenting food-type volatiles such as fermenting bread dough. Analogues of pheromones that strongly reduce response to pheromones by insects might be useful as biochemical probes to study the pharmacophoric (three-dimensional structure) requirements for pheromone perception.

  DOI：

  10.1021/jf9809378
• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 、 2-膦酰丁酸三乙脂 生成 (2E,4E)-2-Ethyl-4-methyl-hexa-2,4-dienoic acid ethyl ester
  参考文献：
  名称：

  Reduction of Carpophilus freemani Dobson (Coleoptera:  Nitidulidae) Aggregation Pheromone Response by Synthetic Analogues

  摘要：

  Analogues of (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene the major component of the aggregation pheromone of Carpophilus freemani Dobson (Coleoptera: Nitidulidae), were synthesized and the potency of these compounds in suppressing the response of C. freemani to its pheromone in a wind tunnel bioassay was determined. The most potent compounds reduced behavioral response to pheromone 83-96% when the inhibitors were present in 10-fold excess. These compounds are (1Z,3E,5E)-1-methoxy-3-ethyl-5-methyl-1,3,5-heptatriene, (1E,3E,5E)- 1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene, and (1Z,3E,5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene. In the presence of fermenting bread dough (a pheromone synergist), the most potent inhibitory compound, (IZ,3E,5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene, was less effective in reducing mean landings (69% vs 99%) than when dough was absent. This inhibitory compound causes a reduction of response to pheromone but does not cause a reduction of response to fermenting food-type volatiles such as fermenting bread dough. Analogues of pheromones that strongly reduce response to pheromones by insects might be useful as biochemical probes to study the pharmacophoric (three-dimensional structure) requirements for pheromone perception.

  DOI：

  10.1021/jf9809378