1-((6-chloropyridin-3-yl)methyl)-8-nitro-7-propyl-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol | 948994-33-0

• 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)-8-nitro-7-propyl-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol
• 英文别名: 1-[(6-chloropyridin-3-yl)methyl]-8-nitro-7-propyl-3,5,6,7-tetrahydro-2H-imidazo[1,2-a]pyridin-5-ol
• CAS: 948994-33-0
• 化学式: C₁₆H₂₁ClN₄O₃
• 分子量: 352.821
• InChiKey: PWEBRGHKELGZDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 1-((6-chloropyridin-3-yl)methyl)-8-nitro-7-propyl-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 1-((6-chloropyridin-3-yl)methyl)-5-methoxy-7-propyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine
  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
• 作为产物：
  描述：

  己烯醛 、 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， 生成 1-((6-chloropyridin-3-yl)methyl)-8-nitro-7-propyl-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

• Organocatalytic Michael addition of 2-nitro methylene imidazolidines to α,β-unsaturated aldehydes: concise synthesis of chiral insecticide Paichongding
  作者：Yanpeng Lou、Yin Xu、Zhuo Chai、Xusheng Shao、Gang Zhao、Zhong Li

  DOI：10.1016/j.tet.2015.07.056

  日期：2015.9

  An organocatalytic Michael reaction of 2-nitro methylene imidazolidines to α,β-unsaturated aldehydes followed by acetal-amination affords hexahydroimidazo[1,2-a]pyridines in high yields and with moderate to excellent enantioselectivity. The utility of the reaction was illustrated by a one-step transformation to Paichongding, an insecticide of the neonicotinoid family.

  2-硝基亚甲基咪唑烷对α，β-不饱和醛的有机催化迈克尔反应，然后进行乙缩醛胺化，可高产率地得到六氢咪唑并[1,2- a ]吡啶，并且具有中等至优异的对映选择性。通过一步转化为新烟碱类杀虫剂Paichongding可以说明该反应的实用性。