1-((6-chloropyridin-3-yl)methyl)-5-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol | 1099832-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 1-((6-chloropyridin-3-yl)methyl)-5-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol
• 英文别名: 1-[(6-Chloropyridin-3-yl)methyl]-5-methyl-8-nitro-2,3,6,7-tetrahydroimidazo[1,2-a]pyridin-5-ol
• CAS: 1099832-22-0
• 化学式: C₁₄H₁₇ClN₄O₃
• 分子量: 324.767
• InChiKey: BQZFIGGVWFAVCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丁烯酮 、 2-氯-5-[[(2Z)-2-(硝基亚甲基)咪唑烷-1-基]甲基]吡啶 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 以53%的产率得到1-((6-chloropyridin-3-yl)methyl)-5-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol
  参考文献：
  名称：

  cis-Nitromethylene neonicotinoids as new nicotinic family: Synthesis, structural diversity, and insecticidal evaluation of hexahydroimidazo[1,2-α]pyridine

  摘要：

  A series of neonicotinoids analogues of hexahydroimidazo[1,2-alpha]pyridine were modified at 5-, 6-, and 7-positions, and their insecticidal activities were evaluated. Introducing a methyl or ethyl at 7-position increased the insecticidal activities, while other substituents decreased activities. When alkyl substituents were introduced to 7-position, the insecticidal activities against Pea aphids decreased in the order methyl (7a) > ethyl (7b) > n-butyl (7e) > phenyl (7f) > n-propyl (7c) > iso-propyl (7d), p-NO2-phenyl (7g). Modifications at 5-, 6- or both at 6- and 7-positions with methyl or ethyl were unfavorable to activities. Interestingly, introducing methyl to 7-position not only increased insecticidal activities against pea aphids, but also show higher insecticidal activities than imidacloprid against imidacloprid-resistant brown planthopper. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.048

文献信息

• cis-Nitromethylene neonicotinoids as new nicotinic family: Synthesis, structural diversity, and insecticidal evaluation of hexahydroimidazo[1,2-α]pyridine
  作者：Xusheng Shao、Wenwen Zhang、Yanqing Peng、Zhong Li、Zhongzhen Tian、Xuhong Qian

  DOI：10.1016/j.bmcl.2008.10.048

  日期：2008.12

  A series of neonicotinoids analogues of hexahydroimidazo[1,2-alpha]pyridine were modified at 5-, 6-, and 7-positions, and their insecticidal activities were evaluated. Introducing a methyl or ethyl at 7-position increased the insecticidal activities, while other substituents decreased activities. When alkyl substituents were introduced to 7-position, the insecticidal activities against Pea aphids decreased in the order methyl (7a) > ethyl (7b) > n-butyl (7e) > phenyl (7f) > n-propyl (7c) > iso-propyl (7d), p-NO2-phenyl (7g). Modifications at 5-, 6- or both at 6- and 7-positions with methyl or ethyl were unfavorable to activities. Interestingly, introducing methyl to 7-position not only increased insecticidal activities against pea aphids, but also show higher insecticidal activities than imidacloprid against imidacloprid-resistant brown planthopper. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.