α-cyano-3-phenoxybenzyl (+/-)-cis,trans-3-(2,5-dioxo-3-cyclopenten-1-ylidenemethyl)-2,2-dimethylcyclopropanecarboxylate

• 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: α-cyano-3-phenoxybenzyl (+/-)-cis,trans-3-(2,5-dioxo-3-cyclopenten-1-ylidenemethyl)-2,2-dimethylcyclopropanecarboxylate
• 英文别名: [Cyano-(3-phenoxyphenyl)methyl] 3-[(2,5-dioxocyclopent-3-en-1-ylidene)methyl]-2,2-dimethylcyclopropane-1-carboxylate
• 化学式: C₂₆H₂₁NO₅
• 分子量: 427.456
• InChiKey: PGOOLWXJQGRELT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  93.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  三苯氧基苯甲醛 在 4-二甲氨基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 β-丙氨酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 21.0h， 生成 α-cyano-3-phenoxybenzyl (+/-)-cis,trans-3-(2,5-dioxo-3-cyclopenten-1-ylidenemethyl)-2,2-dimethylcyclopropanecarboxylate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Pyrethroids Having Halogen, Keto, or Nitro Group-Containing Substituents

  摘要：

  Thirteen pyrethroid esters, most of which contain strong electron-withdrawing groups (e.g., halomethylketo and nitro groups) in the side chain of the cyclopropane acid moiety, have been synthesized. The synthesis involved the reaction of various active methylene compounds with 3-formyl-2,2-dimethylcyclopropanecarboxylic esters of known pyrethroid alcohols. Rather than the usually employed Wittig reaction for these syntheses, the novel pyrethroid acid moieties were prepared by amino acid-catalyzed Knoevenagel condensations under mild conditions. Preliminary toxicity studies of the pyrethroid esters, against several insect and one mite species, were conducted. Two of these compounds had good repellent activity against the twospotted spider mite (Tetranychus urticae) at 100 ppm, and six of them had medium insecticidal activity against either black bean aphid (Aphis fabae) or western potato leafhopper (Empoasca abrupta) at 10 ppm.

  DOI：

  10.1021/jf00056a060

文献信息

• Synthesis and Biological Evaluation of New Pyrethroids Having Halogen, Keto, or Nitro Group-Containing Substituents
  作者：Ming-Kuan Chyan、Scott J. Norton

  DOI：10.1021/jf00056a060

  日期：1995.8

  Thirteen pyrethroid esters, most of which contain strong electron-withdrawing groups (e.g., halomethylketo and nitro groups) in the side chain of the cyclopropane acid moiety, have been synthesized. The synthesis involved the reaction of various active methylene compounds with 3-formyl-2,2-dimethylcyclopropanecarboxylic esters of known pyrethroid alcohols. Rather than the usually employed Wittig reaction for these syntheses, the novel pyrethroid acid moieties were prepared by amino acid-catalyzed Knoevenagel condensations under mild conditions. Preliminary toxicity studies of the pyrethroid esters, against several insect and one mite species, were conducted. Two of these compounds had good repellent activity against the twospotted spider mite (Tetranychus urticae) at 100 ppm, and six of them had medium insecticidal activity against either black bean aphid (Aphis fabae) or western potato leafhopper (Empoasca abrupta) at 10 ppm.