2-[2-oxa-(Z)-6-undecenyl]-isoindole-1,3-dione | 202473-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[2-oxa-(Z)-6-undecenyl]-isoindole-1,3-dione
• CAS: 202473-36-7
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: XXBZBQVJRSMBGP-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[2-oxa-(Z)-6-undecenyl]-isoindole-1,3-dione 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 水 、 对甲苯磺酸 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 异丙醇 、 丙酮 、 苯 为溶剂， 反应 9.0h， 生成 2-Methyl-5-[(Z)-4-nonenyl]-oxazole
  参考文献：
  名称：

  Bioisosteric Approach to Elucidation of Binding of the Acetate Group of a Moth Sex Pheromone Component to Its Receptor

  摘要：

  A number of analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, in which the acetate group has been replaced by functional groups that may function as bioisosters, have been synthesized and tested using single-cell electrophysiology. The activities have been interpreted in terms of the molecular electrostatic potentials of the polar functional group as calculated by ab initio quantum mechanical calculations. It is concluded that both oxygens of the acetate group in (Z)-5-decenyl acetate contribute to the interactions between the pheromone component and its receptor. Furthermore, the results indicate that the crucial interaction between the carbonyl group and the receptor, which is most probably a hydrogen bonding interaction, takes place in a direction pointing away from the hydrocarbon chain of the pheromone component.

  DOI：

  10.1023/a:1022563010599
• 作为产物：
  描述：

  邻苯二甲酰甘氨酸 在 草酰氯 、 lithium 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 2-[2-oxa-(Z)-6-undecenyl]-isoindole-1,3-dione
  参考文献：
  名称：

  Bioisosteric Approach to Elucidation of Binding of the Acetate Group of a Moth Sex Pheromone Component to Its Receptor

  摘要：

  A number of analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, in which the acetate group has been replaced by functional groups that may function as bioisosters, have been synthesized and tested using single-cell electrophysiology. The activities have been interpreted in terms of the molecular electrostatic potentials of the polar functional group as calculated by ab initio quantum mechanical calculations. It is concluded that both oxygens of the acetate group in (Z)-5-decenyl acetate contribute to the interactions between the pheromone component and its receptor. Furthermore, the results indicate that the crucial interaction between the carbonyl group and the receptor, which is most probably a hydrogen bonding interaction, takes place in a direction pointing away from the hydrocarbon chain of the pheromone component.

  DOI：

  10.1023/a:1022563010599