| 1404333-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• CAS: 1404333-20-5
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: SJAUCBISAVTMSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.1
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3-三氟甲基苄基)-肼 、 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 N-[4-chloro-2-[[[3-(trifluoromethyl)phenyl]methylamino]carbamoyl]phenyl]-2,2-dimethylpropanamide
  参考文献：
  名称：

  Synthesis and Bioactivity Study of 2-Acylamino-Substituted N′-Benzylbenzohydrazide Derivatives

  摘要：

  The discovery of new safe and effective pesticides is one of the main means of providing eco-friendly agricultural agents for modern crop protection. To identify new biological molecules based of the anthranilic diamide skeleton of the novel pesticide chlorantraniliprole, which acts on the ryanodine receptor and functional groups in acyl hydrazine insect growth regulators, more than 40 new compounds of 2-acylamino-substituted N'-benzylbenzohydrazide derivatives were designed and synthesized. The structures of the new compounds were characterized using H-1 nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), or electron impact mass spectrometry (El MS), and their biological activities at a concentration of 600 mg L-1 were determined against cotton aphid (Aphis gossypii Glover), carmine spider mite (Tetranychus cinnabarinus), and diamondback moth (Plutella xylostella). The results of a preliminary assay showed that compounds 6a-I-2 and 6d-III-4 maintained the lethal activity of anthranilic diamide against P. xylostella; compounds 6c-II-4, 6d-I-7, 6d-II-1, and 6d-III-5 exhibited good lethal activity against A gossypii; and compounds 6a-II-1, 6a-III-1, 6b-I-7, 6c-I-1, and 6c-III-5 retained promising larvicidal activities against T. cinnabarinus. In subsequent further tests against T. cinnabarinus, compounds 6a-II-1, 6a-III-1, 6c-I-1, and 6c-III-5 showed an LC50 value of <90 mg L-1; especially, the LC50 of compound 6a-III-1 was only 27.9 mg L-1. In conclusion, the introduction of the functional fragment-substituted acyl hydrazine improved the acaricidal activity of the anthranilic diamide skeleton, and the halogen atom at X position and the methyl group at RI play crucial roles in the biological activities of the compounds.

  DOI：

  10.1021/jf303376t
• 作为产物：
  描述：

  5-氯靛红酸酐 、 三甲基乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.17h， 以81%的产率得到
  参考文献：
  名称：

  Synthesis and Bioactivity Study of 2-Acylamino-Substituted N′-Benzylbenzohydrazide Derivatives

  摘要：

  The discovery of new safe and effective pesticides is one of the main means of providing eco-friendly agricultural agents for modern crop protection. To identify new biological molecules based of the anthranilic diamide skeleton of the novel pesticide chlorantraniliprole, which acts on the ryanodine receptor and functional groups in acyl hydrazine insect growth regulators, more than 40 new compounds of 2-acylamino-substituted N'-benzylbenzohydrazide derivatives were designed and synthesized. The structures of the new compounds were characterized using H-1 nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), or electron impact mass spectrometry (El MS), and their biological activities at a concentration of 600 mg L-1 were determined against cotton aphid (Aphis gossypii Glover), carmine spider mite (Tetranychus cinnabarinus), and diamondback moth (Plutella xylostella). The results of a preliminary assay showed that compounds 6a-I-2 and 6d-III-4 maintained the lethal activity of anthranilic diamide against P. xylostella; compounds 6c-II-4, 6d-I-7, 6d-II-1, and 6d-III-5 exhibited good lethal activity against A gossypii; and compounds 6a-II-1, 6a-III-1, 6b-I-7, 6c-I-1, and 6c-III-5 retained promising larvicidal activities against T. cinnabarinus. In subsequent further tests against T. cinnabarinus, compounds 6a-II-1, 6a-III-1, 6c-I-1, and 6c-III-5 showed an LC50 value of <90 mg L-1; especially, the LC50 of compound 6a-III-1 was only 27.9 mg L-1. In conclusion, the introduction of the functional fragment-substituted acyl hydrazine improved the acaricidal activity of the anthranilic diamide skeleton, and the halogen atom at X position and the methyl group at RI play crucial roles in the biological activities of the compounds.

  DOI：

  10.1021/jf303376t

文献信息

• Construction of Benzoxazinones from Anilines and Their Derivatives
  作者：Teng-Fei Zhao、Xiao-Li Xu、Wei-Yin Sun、Yi Lu

  DOI：10.1021/acs.orglett.3c01511

  日期：2023.7.14

  Herein we report a strategy concerning Rh(III)-catalyzed direct ortho-C–H bond carbonylation to construct benzoxazinones from anilines and their derivatives with high atom economy. Interestingly, the corresponding amides were generated in situ from anilines when excess Ac2O was added and directed the following C–H bond carbonylation to form benzoxazinones. Extensive functional group tolerance can be

  在此，我们报道了一种Rh(III)催化的直接邻-C-H键羰基化反应，以苯胺及其高原子经济性衍生物构建苯并恶嗪酮的策略。有趣的是，当添加过量的Ac 2 O时，苯胺原位生成相应的酰胺，并引导随后的C-H键羰基化形成苯并恶嗪酮。当安装烷基酰胺导向基团时，可以实现广泛的官能团耐受性。此外，该方法可以方便地对一些带有芳胺基团的药物进行衍生化，显示出其潜在的应用前景。