1-((6-chloropyridin-3-yl)methyl)-5-methyl-7-nitro-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole-5,6-diol | 1417509-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-((6-chloropyridin-3-yl)methyl)-5-methyl-7-nitro-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole-5,6-diol
• 英文别名: 1-[(6-chloropyridin-3-yl)methyl]-5-methyl-7-nitro-3,6-dihydro-2H-pyrrolo[1,2-a]imidazole-5,6-diol
• CAS: 1417509-19-3
• 化学式: C₁₃H₁₅ClN₄O₄
• 分子量: 326.739
• InChiKey: LGWYUUYJKRTMFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-((6-chloropyridin-3-yl)methyl)-5-methyl-7-nitro-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole-5,6-diol 在 aluminum (III) chloride 作用下， 以 甲醇 、 丙酮 为溶剂， 以63%的产率得到1-((6-chloropyridin-3-yl)methyl)-5-methyl-7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]imidazol-6(5H)-one
  参考文献：
  名称：

  Pyrrole- and Dihydropyrrole-Fused Neonicotinoids: Design, Synthesis, and Insecticidal Evaluation

  摘要：

  Versatile pyrrole- and dihydropyrrole-fused neonicotinoids were obtained from cyclic and non-cyclic nitroeneamines. Anhydrous aluminum chloride (AlCl3) exhibited high catalytic selectivity for the synthesis of the titled etherified compounds at room temperature and the eliminated products under reflux conditions. The target molecules have been identified on the basis of satisfactory analytical and spectral [H-1 and C-13 nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HAMS), and X-ray] data. All synthesized compounds have been screened for insecticidal activity. The preliminary insecticidal activity results showed that some of the aimed compounds displayed excellent insecticidal activity against cowpea aphids (Aphis craccivora).

  DOI：

  10.1021/jf3044132
• 作为产物：
  描述：

  2-氯-5-[[(2Z)-2-(硝基亚甲基)咪唑烷-1-基]甲基]吡啶 、 丙酮醛 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到1-((6-chloropyridin-3-yl)methyl)-5-methyl-7-nitro-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole-5,6-diol
  参考文献：
  名称：

  Pyrrole- and Dihydropyrrole-Fused Neonicotinoids: Design, Synthesis, and Insecticidal Evaluation

  摘要：

  Versatile pyrrole- and dihydropyrrole-fused neonicotinoids were obtained from cyclic and non-cyclic nitroeneamines. Anhydrous aluminum chloride (AlCl3) exhibited high catalytic selectivity for the synthesis of the titled etherified compounds at room temperature and the eliminated products under reflux conditions. The target molecules have been identified on the basis of satisfactory analytical and spectral [H-1 and C-13 nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HAMS), and X-ray] data. All synthesized compounds have been screened for insecticidal activity. The preliminary insecticidal activity results showed that some of the aimed compounds displayed excellent insecticidal activity against cowpea aphids (Aphis craccivora).

  DOI：

  10.1021/jf3044132

文献信息

• [EN] PREPARATION AND USE OF PYRROLE AND DIHYDROPYRROLE FUSED RING COMPOUND HAVING INSECTICIDAL ACTIVITY<br/>[FR] PRÉPARATION ET UTILISATION D'UN COMPOSÉ À CYCLE CONDENSÉ DE PYRROLE ET DE DIHYDROPYRROLE PRÉSENTANT UNE ACTIVITÉ INSECTICIDE
  申请人：UNIV EAST CHINA SCIENCE & TECH

  公开号：WO2013007168A1

  公开（公告）日：2013-01-17

  本发明提供了具有杀虫活性的吡咯及二氢吡咯稠环化合物的制备与用途。具体的，本发明涉及具有通式（A）所示的化合物或者该类化合物的光学异构体、顺反异构体或农药学上可接受的盐，及其制备方法。本发明还涉及包含上述化合物、或其光学异构体、顺反异构体或农药学上可接受的盐的农用组合物及其用途。所述化合物及其衍生物对同翅目、鳞翅目等农林业害虫，如蚜虫、飞虱、粉虱、叶蝉、蓟马、棉铃虫、菜青虫、小菜蛾、斜纹夜蛾、粘虫等具有高杀虫活性。
• Pyrrole- and Dihydropyrrole-Fused Neonicotinoids: Design, Synthesis, and Insecticidal Evaluation
  作者：Zhenjun Ye、Lina Shi、Xusheng Shao、Xiaoyong Xu、Zhiping Xu、Zhong Li

  DOI：10.1021/jf3044132

  日期：2013.1.16

  Versatile pyrrole- and dihydropyrrole-fused neonicotinoids were obtained from cyclic and non-cyclic nitroeneamines. Anhydrous aluminum chloride (AlCl3) exhibited high catalytic selectivity for the synthesis of the titled etherified compounds at room temperature and the eliminated products under reflux conditions. The target molecules have been identified on the basis of satisfactory analytical and spectral [H-1 and C-13 nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HAMS), and X-ray] data. All synthesized compounds have been screened for insecticidal activity. The preliminary insecticidal activity results showed that some of the aimed compounds displayed excellent insecticidal activity against cowpea aphids (Aphis craccivora).