2-chloro-5-(((E)-2-(((E)-mesityldiazenyl)(nitro)methylene)imidazolidin-1-yl)methyl)thiazole | 1335228-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-chloro-5-(((E)-2-(((E)-mesityldiazenyl)(nitro)methylene)imidazolidin-1-yl)methyl)thiazole
• CAS: 1335228-71-1
• 化学式: C₁₇H₁₉ClN₆O₂S
• 分子量: 406.896
• InChiKey: BHMJZYIVETYQCS-DYUKIBRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  96.02
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (E)-2-chloro-5-((2-(nitromethylene)imidazolidin-1-yl)methyl)thiazole 、 2,4,6-三甲基苯胺 在 盐酸 、 sodium nitrite 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 以70%的产率得到2-chloro-5-(((E)-2-(((E)-mesityldiazenyl)(nitro)methylene)imidazolidin-1-yl)methyl)thiazole
  参考文献：
  名称：

  Design, Synthesis, Crystal Structure Analysis, and Insecticidal Evaluation of Phenylazoneonicotinoids

  摘要：

  On the basis of research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a series of phenylazoneonicotinoids were designed and synthesized to further promote the pi-pi interaction between molecule and amino acid residues. The target compounds have been identified on the basis of satisfactory analytical and spectral (H-1 NMR, C-13 NMR, HRMS, and X-ray) data. The preliminary results revealed that tiny differences in substitutes resulted in different configurations and great bioactivity variations. Some compounds with electron-donating groups on positions 2 and 6 of the phenyl ring presented higher insecticidal activity than imidacloprid against cowpea aphids (Aphis craccivora). The impressive crystal structure of the excellent insecticidal activity compound 9q clearly proved that the functional electronegative pharmacophore was approximately vertical to the methyleneimidazolidine plane. The differences in the mode of interaction on nAChR of typical compounds 9h and 9q remain unclear.

  DOI：

  10.1021/jf2029708