5-((2-(nitromethylene)imidazolidin-1-yl)methyl)pyridine | 100553-56-8

• 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: 5-((2-(nitromethylene)imidazolidin-1-yl)methyl)pyridine
• 英文别名: 1-(3-pyridyl)methyl-2-nitromethylene-imidazolidine；1-(nicotinyl)-2-nitromethyleneimidazolidine；1-(5-Pyridylmethyl)-2-(nitromethylene)imidazolidine；3-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyridine
• CAS: 100553-56-8
• 化学式: C₁₀H₁₂N₄O₂
• 分子量: 220.231
• InChiKey: PWHOPRHAWMKNIM-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  408.3±45.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-((2-(nitromethylene)imidazolidin-1-yl)methyl)pyridine 在 溴 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 4.34h， 生成 (E)-2-nitro-2-[1-(3-pyridinylmethyl)-2-imidazolidinylidene]acetonitrile
  参考文献：
  名称：

  Design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides

  摘要：

  A series of cyanonitrovinyl neonicotinoids were designed and synthesized via five steps in about 35% overall yields. All compounds were structurally characterized by (1)H nuclear magnetic resonance (NMR), (13)C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction analysis of 2-[1-[(6-chloropyridin-3-yl)methyl]-2-imidazolidinylidene]-2-nitroacetonitrile revealed that the double bond is (E)-configured. The preliminary agriculture bioassay indicated that one compound exhibited moderate insecticidal activity against pea aphid.

  DOI：

  10.1007/s00706-010-0375-4
• 作为产物：
  描述：

  3-氯甲基吡啶 以 乙醇 、 乙腈 为溶剂， 生成 5-((2-(nitromethylene)imidazolidin-1-yl)methyl)pyridine
  参考文献：
  名称：

  Design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides

  摘要：

  A series of cyanonitrovinyl neonicotinoids were designed and synthesized via five steps in about 35% overall yields. All compounds were structurally characterized by (1)H nuclear magnetic resonance (NMR), (13)C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction analysis of 2-[1-[(6-chloropyridin-3-yl)methyl]-2-imidazolidinylidene]-2-nitroacetonitrile revealed that the double bond is (E)-configured. The preliminary agriculture bioassay indicated that one compound exhibited moderate insecticidal activity against pea aphid.

  DOI：

  10.1007/s00706-010-0375-4

文献信息

• One step from nitro to oxime: a convenient preparation of unsaturated oximes by the reduction of the corresponding vinylnitro compounds
  作者：Kewei Wang、Xuhong Qian、Jingnan Cui

  DOI：10.1016/j.tet.2009.10.042

  日期：2009.12

  A series of novel unsaturated oximes were conveniently prepared from the corresponding vinylnitro compounds by reduction with SnCl2·2H2O. The structures of the oximes were characterized by 1H and 13C NMR, IR and HRMS, and X-ray crystallography analysis of 1-(6-chloro-pyridin-3-ylmethyl)-4,5-dihydro-1H-imidazole-2-carbaldehyde oxime 2a reveals that, the hydroxyl group is arranged in a trans configuration

  可以通过相应的乙烯基硝基化合物通过SnCl 2 ·2H 2 O还原而方便地制备一系列新型不饱和肟。肟的结构通过1 H和13 C NMR，IR和HRMS以及X射线晶体学分析进行表征。 1-（6-氯-吡啶-3-基甲基）-4，5-二氢-1H-咪唑-2-甲醛甲醛肟2a表明，羟基以反式构型排列。简短调查的一些证据表明，这些肟似乎是由硝基脂族化合物的aci形式还原而形成的。
• Synthesis, crystal structure, and biological evaluation of a novel eight-membered dinitration neonicotinoid analogues
  作者：Xiao Zhang、Weiwei Yu、Xiaoyong Xu、Xusheng Shao、Zhong Li

  DOI：10.1016/j.bmcl.2021.127960

  日期：2021.7

  intermediate synthesis, a serendipitous reaction of introducing nitro group from nitromethylene has been observed. Instead of expected dihydroxy compounds, dinitration structures with nitromethylene analogues were prepared under mild conditions by using a metal-free catalyst B(OH)3. In this reaction, the extra nitro group was suggested to be from starting material. Bioassays indicated that compound 3a showed

  在二羟基中间体合成的研究中，观察到从硝基亚甲基引入硝基的偶然反应。代替预期的二羟基化合物，使用无金属催化剂 B(OH) 3在温和条件下制备了具有硝基亚甲基类似物的二硝化结构。在该反应中，建议额外的硝基来自起始材料。生物测定表明，化合物3a对豇豆蚜虫（Aphis craccivora）和粘虫（Mythimna separata）表现出良好的杀虫活性，LC 50值分别为4.9 mg/L和7.1 mg/L。
• 具有杀虫活性的含氮桥环化合物及其制备和 用途
  申请人：华东理工大学

  公开号：CN105461724B

  公开（公告）日：2019-11-05

  本发明涉及具有杀虫活性的含氮桥环化合物及其制备和用途。具体地，本发明提供了通式1所示结构的化合物及其制备方法和用途，式中R1、R2、R3、R4、R5、R6、R7、R8、R、n、Z各自如说明书中所述定义。本发明还涉及包含上述化合物或农药学上可接受的盐的农用组合物，所述农用组合物的用途。所述化合物对同翅目、鳞翅目等农林业害虫，例如蚜虫、飞虱、粉虱、叶蝉、蓟马、棉铃虫、菜青虫、小菜蛾、斜纹夜蛾、粘虫等具有高的杀虫活性。
• Heterocyclic compounds
  申请人：Nihon Bayer Agrochem K.K.

  公开号：US06022967A1

  公开（公告）日：2000-02-08

  Novel insecticides of the formula ##STR1## in which n is 0 or 1, X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.

  化学式为##STR1##的新型杀虫剂，其中n为0或1，X为S、O、##STR2##，Y为N或##STR3##，Z为含氮的5-或6元杂环，R至R.sup.9分别表示氢或特定的有机基团。
• Moriya, Koichi; Shibuya, Katsuhiko; Hattori, Yumi, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 1, p. 127 - 128
  作者：Moriya, Koichi、Shibuya, Katsuhiko、Hattori, Yumi、Tsuboi, Shin-ichi、Shiokawa, Kozo、Kagabu, Shinzo

  DOI：——

  日期：——