1-((6-chloropyridin-3-yl)methyl)-8-nitro-7-phenyl-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol | 948994-58-9

• 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-phenyl-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-phenyl-3,5,6,7-tetrahydro-2H-imidazo[1,2-a]pyridin-5-ol
• CAS: 948994-58-9
• 化学式: C₁₉H₁₉ClN₄O₃
• 分子量: 386.838
• InChiKey: RHQQBOMMVMDSSA-UHFFFAOYSA-N

物化性质

• 熔点：
  229.3-230.1 °C
• 沸点：
  590.9±50.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 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-phenyl-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-phenyl-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：

  2-氯-5-[[(2Z)-2-(硝基亚甲基)咪唑烷-1-基]甲基]吡啶 、 肉桂醛 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以40%的产率得到1-((6-chloropyridin-3-yl)methyl)-8-nitro-7-phenyl-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol
  参考文献：
  名称：

  PREPARATION METHOD AND USE OF COMPOUNDS HAVING HIGH INSECTICIDAL ACTIVITIES

  摘要：

  本发明公开了一种亚硝基甲烯衍生物，以及它们的制备方法和用途。杀虫活性测试表明，本发明的亚硝基甲烯衍生物不仅对具有刺吸型或擦伤型口器的昆虫（如蚜虫、叶蝉、植食蝗、蓟马和烟粉虱及其抗性品系）表现出高杀虫活性，而且对水稻纵卷叶象、胭脂蜘蛛螨等也表现出高杀虫活性，它们还可用于预防卫生害虫和白蚁。

  公开号：

  US20090111847A1

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。
• PREPARATION METHOD AND USE OF COMPOUNDS HAVING HIGH BIOCIDAL ACTIVITIES
  申请人：East China University of Science and Technology

  公开号：EP1997820A1

  公开（公告）日：2008-12-03

  The present invention discloses a kind of nitromethylene derivatives as well as their preparation method and their uses. The insecticidal activity tests show that the nitromethylene derivatives of the present invention not only show high insecticidal activities against insects with piercing-sucking type or scratching type mouthparts, such as aphid, leafhoppei, plant hopper, thrips and white fly and their resistant strains, but also show high insecticidal activities against Lissorhoptrus oryzophilus, carmine spider mite, and they can also be used to prevent sanitary pest, and white ant.

  本发明公开了一种硝基亚甲基衍生物及其制备方法和用途。杀虫活性试验表明，本发明的硝基亚甲基衍生物不仅对蚜虫、叶蝉、植物跳虫、蓟马、白粉虱等具有刺吸式或搔抓式口器的昆虫及其抗性品系有较高的杀虫活性，而且对蚜小蜂、胭脂蛛螨也有较高的杀虫活性，还可用于防治卫生害虫和白蚁。
• EP1997820
  申请人：——

  公开号：——

  公开（公告）日：——
• PREPARATION METHOD AND USE OF COMPOUNDS HAVING HIGH INSECTICIDAL ACTIVITIES
  申请人：Li Zhong

  公开号：US20090111847A1

  公开（公告）日：2009-04-30

  The present invention discloses a kind of nitromethylene derivatives as well as their preparation method and their uses. The insecticidal activity tests show that the nitromethylene derivatives of the present invention not only show high insecticidal activities against insects with piercing-sucking type or scratching type mouthparts, such as aphid, leafhopper, plant hopper, thrips and white fly and their resistant strains, but also show high insecticidal activities against Lissorhoptrus oryzophilus , carmine spider mite, and they can also be used to prevent sanitary pest, and white ant.

  本发明公开了一种亚硝基甲烯衍生物，以及它们的制备方法和用途。杀虫活性测试表明，本发明的亚硝基甲烯衍生物不仅对具有刺吸型或擦伤型口器的昆虫（如蚜虫、叶蝉、植食蝗、蓟马和烟粉虱及其抗性品系）表现出高杀虫活性，而且对水稻纵卷叶象、胭脂蜘蛛螨等也表现出高杀虫活性，它们还可用于预防卫生害虫和白蚁。
• 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.