2,4-dichloro-3-nitroaniline | 129825-24-7

• 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: 2,4-dichloro-3-nitroaniline
• 英文别名: 2.5-Dichlor-4-nitro-anilin；2,4-Dichlor-3-nitro-anilin
• CAS: 129825-24-7
• 化学式: C₆H₄Cl₂N₂O₂
• 分子量: 207.016
• InChiKey: FWIXWQXCEXDFAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.16
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-3-nitroaniline 在 盐酸 、 tin 作用下， 生成 2,6-二氯苯胺
  参考文献：
  名称：

  Koerner; Contardi, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1909, vol. <5> 18 I, p. 100

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2,4-dichloro-3-nitrophenyl)pyridin-1-ium trifluoromethanesulfonate 在 哌啶 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 3,5-dichloro-4-nitroaniline 、 2,4-dichloro-3-nitroaniline
  参考文献：
  名称：

  芳烃CH氨基化的吡啶基自由基阳离子

  摘要：

  电子转移光催化使人们可以从选定的N-取代的吡啶鎓试剂中获得难以捉摸的N-吡啶基自由基阳离子。所得的（杂）芳烃的C（sp 2）-H功能化为开发有价值的胺化芳基骨架提供了多种中间体。包括第一个光谱学证据的自旋捕获的N-吡啶基自由基加合物的机理研究表明，SET触发了由可见光介导的N-X吡啶鎓试剂的伪介观裂解。

  DOI：

  10.1002/anie.201810261

文献信息

• Discovery of a polysubstituted phenyl containing novel N-phenylpyrazole scaffold as potent ryanodine receptor activator
  作者：Jingbo Liu、Fengyun Li、Zesheng Hao、Yuanhong Wang、Xuewen Hua、Yuxin Li、Zhengming Li

  DOI：10.1016/j.bmc.2020.115829

  日期：2020.12

  To develop the novel ryanodine receptors (RyRs) insecticides, encouraged by our previous research work, a series of novel N-phenylpyrazole derivatives containing a polysubstituted phenyl ring scaffold were designed and synthesized. The bioassays results indicated that some title compounds exhibited excellent insecticidal activity. For oriental armyworm (Mythimna separata), compounds 7f, 7g, 7i and 7o at 0.5 mg L^-1 displayed 100% larvicidal activity, and even at 0.1 mg L^-1, 7o was 30% larvicidal activity, comparable to chlorantraniliprole (30%) and better than cyantraniliprole (10%). Compounds 7f and 7o had the median lethal concentrations (LC₅₀) of 8.83 × 10^-2 and 7.12 × 10^-2 mg L^-1, respectively, close to chlorantraniliprole (6.79 × 10^-2 mg L^-1). Additionally, for diamondback moth (Plutella xylostella), the larvicidal activity of compounds 7f and 7i were 90% and 70% at 0.01 mg L^-1, respectively, better than chlorantraniliprole (50%) and cyantraniliprole (40%). More impressively, the LC₅₀ value of 7f was 4.2 × 10^-3 mg L^-1, slightly lower than that of chlorantraniliprole (5.0 × 10^-3 mg L^-1). The molecular docking between compound 7f and RyRs of diamondback moth validated our molecular designation. Furthermore, the calcium imaging experiment explored the influence of compound 7o on the calcium homeostasis in the central neurons of the third larvae of oriental armyworm. The results of this study indicated that 7o is a potent novel lead targeting at RyRs.