1-[(6-Chloropyridin-3-yl)methyl]-5-(2-fluoro-4-methylphenyl)-7-(furan-2-yl)-8-nitro-2,3,5,7-tetrahydroimidazo[1,2-a]pyridine-6,6-dicarbonitrile | 1227682-53-2

• 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-(2-fluoro-4-methylphenyl)-7-(furan-2-yl)-8-nitro-2,3,5,7-tetrahydroimidazo[1,2-a]pyridine-6,6-dicarbonitrile
• CAS: 1227682-53-2
• 化学式: C₂₆H₂₀ClFN₆O₃
• 分子量: 518.935
• InChiKey: NHDFZADPCXLXPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N'-((6-chloropyridin-3-yl)methyl)ethane-1,2-diamine 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 生成 1-[(6-Chloropyridin-3-yl)methyl]-5-(2-fluoro-4-methylphenyl)-7-(furan-2-yl)-8-nitro-2,3,5,7-tetrahydroimidazo[1,2-a]pyridine-6,6-dicarbonitrile
  参考文献：
  名称：

  Designing Tetrahydroimidazo[1,2-a]pyridine Derivatives via Catalyst-free Aza-Diels−Alder Reaction (ADAR) and Their Insecticidal Evaluation

  摘要：

  A series of tetrahydroimidazo[1,2-a]pyridine derivatives were synthesized by the reaction of 2-vinyl-4,5-dihydroimidazole derivatives with substituted benzylidenemalononitrile via a catalyst-free aza-Diels-Alder reaction. Insecticidal activities of target compounds were tested against pea aphids (Aphis craccivora), which showed that activities were strongly influenced by the substituents and their positions. Especially, the introduction of a fluoro group at the 2- position increased activities.

  DOI：

  10.1021/jf100645y

文献信息

• Facile three-component synthesis and insecticidal evaluation of hexahydroimidazo[1,2-a]pyridine derivatives
  作者：Ye-Feng Fan、Wen-Wen Zhang、Xu-Sheng Shao、Zhi-Ping Xu、Xiao-Yong Xu、Zhong Li

  DOI：10.1016/j.cclet.2014.10.019

  日期：2015.1

  A series of new hexahydroimidazo[1,2-a]pyridine derivatives were synthesized via convenient and practical three-component reactions. Preliminary bioassays showed that majority of the target compounds exhibited moderate to excellent insecticidal activity against cowpea aphids (Aphis craccivora). Among them, compound 9I demonstrated significant activity with LC50 value of 0.00918 mmol/L which was about 3.8-fold higher than that of imidacloprid (IMI). Furthermore, the study of stereostructure-activity relationship of four isomers of 9k indicated that configuration played a key role in insecticidal activity of these compounds. (C) 2014 Zhong Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.