4-bromo-2-(α-chloro-4-chlorobenzyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile | 1614231-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-2-(α-chloro-4-chlorobenzyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
• 英文别名: 4-bromo-2-[chloro-(4-chlorophenyl)methyl]-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
• CAS: 1614231-65-0
• 化学式: C₁₃H₆BrCl₂F₃N₂
• 分子量: 398.009
• InChiKey: CMOJGVTXZDMFQI-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  479.8±45.0 °C(predicted)
• 密度：
  1.77±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(α-chloro-4-chlorobenzyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 7.17h， 生成 4-bromo-1-(ethoxymethyl)-2-(α-(2,2,2-trifluoroethoxy)-4-chlorobenzyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Various α-Substituted Benzylpyrroles Based on the Structures of Insecticidal Chlorfenapyr and Natural Pyrrolomycins

  摘要：

  On the basis of the structures of chlorfenapyr and dioxapyrrolomycin, a series of 2-benzylpyrroles with a hydroxyl, an alkyloxy, an acyloxy, an alkylsulfanyl, or an oxime moiety at the α-position of benzyl were designed and synthesized. Their insecticidal, acaricidal, and fungicidal activities were extensively investigated. The structure-activity relationship showed that benzylpyrroles bearing shorter α-alkyloxy groups gave better activities against most of the insect species; the alkylation of pyrrole usually gave increased activity. Among all compounds, (4-bromo-2-(α-(2,2,2-trifluoroethoxy)-4-chlorobenzyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile) (5'j) exhibited the most outstanding insecticidal activities against oriental armyworm (IC₅₀=10 mg L⁻¹), diamondback moth (0.07 mg L⁻¹), corn borer (50 mg L⁻¹), and mosquito (0.04 mg L⁻¹), which are very close to those of chlorfenapyr (5, 0.08, <25, and <0.025 mg L⁻¹, respectively). In addition, some compounds also exhibited a broad or selective fungicidal spectrum.

  DOI：

  10.1021/jf501377t
• 作为产物：
  描述：

  4-bromo-2-(α-hydroxyl-4-chlorobenzyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以90%的产率得到4-bromo-2-(α-chloro-4-chlorobenzyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Various α-Substituted Benzylpyrroles Based on the Structures of Insecticidal Chlorfenapyr and Natural Pyrrolomycins

  摘要：

  On the basis of the structures of chlorfenapyr and dioxapyrrolomycin, a series of 2-benzylpyrroles with a hydroxyl, an alkyloxy, an acyloxy, an alkylsulfanyl, or an oxime moiety at the α-position of benzyl were designed and synthesized. Their insecticidal, acaricidal, and fungicidal activities were extensively investigated. The structure-activity relationship showed that benzylpyrroles bearing shorter α-alkyloxy groups gave better activities against most of the insect species; the alkylation of pyrrole usually gave increased activity. Among all compounds, (4-bromo-2-(α-(2,2,2-trifluoroethoxy)-4-chlorobenzyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile) (5'j) exhibited the most outstanding insecticidal activities against oriental armyworm (IC₅₀=10 mg L⁻¹), diamondback moth (0.07 mg L⁻¹), corn borer (50 mg L⁻¹), and mosquito (0.04 mg L⁻¹), which are very close to those of chlorfenapyr (5, 0.08, <25, and <0.025 mg L⁻¹, respectively). In addition, some compounds also exhibited a broad or selective fungicidal spectrum.

  DOI：

  10.1021/jf501377t