N-(3-nitro-benzyl)-ethylenediamine | 102495-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-nitro-benzyl)-ethylenediamine
• 英文别名: N-(3-Nitro-benzyl)-aethylendiamin；N'-[(3-nitrophenyl)methyl]ethane-1,2-diamine
• CAS: 102495-23-8
• 化学式: C₉H₁₃N₃O₂
• 分子量: 195.221
• InChiKey: SPSXFJLYRZSJJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-nitro-benzyl)-ethylenediamine 、 1,1-双(甲硫基)-2-亚硝基乙烯 以 乙醇 为溶剂， 生成 1-(3-Nitro-benzyl)-2-[1-nitro-meth-(E)-ylidene]-imidazolidine
  参考文献：
  名称：

  Binding activity of substituted benzyl derivatives of chloronicotinyl insecticides to housefly-head membranes, and its relationship to insecticidal activity against the houseflyMusca domestica

  摘要：

  Variously substituted benzyl derivatives of chloronicotinyl insecticides were synthesized with a wide range of substituents including halogens, NO2, CN, CF, and small alkyl and alkoxy groups at the ortho, meta and para positions, as well as multiple-substituted benzyl analogues. Their binding activity to the alpha-bungarotoxin binding site in housefly (Musca domestica) head membrane preparations was measured. Among the compounds tested, the activity of the meta-CN derivative was the highest, being 20-100 times higher than those of imidacloprid, acetamiprid and nitenpyram. The synergized insecticidal activity against houseflies was also measured for selected compounds with the metabolic inhibitor, NIA16388 (propargyl propyl phenylphosphonate). For the nitromethylene analogues, including both benzyl and pyridylmethyl analogues, higher binding activity usually resulted in higher insecticidal activity. (C) 2000 Society of Chemical Industry.

  DOI：

  10.1002/1526-4998(200010)56:10<875::aid-ps220>3.0.co;2-a
• 作为产物：
  描述：

  3,3'-Me2-salen-H2 在 甲酸 、 N,N'-bis-<3-nitro-benzyl>-ethylenediamine 、 sodium formate 作用下， 生成 N-(3-nitro-benzyl)-ethylenediamine
  参考文献：
  名称：

  Eckstein; Lukasiewicz, Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1959, vol. 7, p. 789,790,795

  摘要：

  DOI：

文献信息

• Synthesis, electrochemistry, and molluscicidal activity of nitroaromatic compounds: effects of substituents and the role of redox potential
  作者：Fabiane C. de Abreu、Francine S. de Paula、Aldenir F. dos Santos、Antônio Euzébio G. Sant'Ana、Mauro V. de Almeida、Eloi T. Cesar、Márcio N. Trindade、Marı́lia O.F. Goulart

  DOI：10.1016/s0968-0896(00)00283-2

  日期：2001.3

  group is important for the biological activity. Correlation with redox potential, however, was not evident. Structural effects seem to be the most important parameter. Higher activity is noticeable for phenols, including the para-nitro azo or hydrazo-containing compounds. No activity was observed for compounds having the benzylic substituent in meta position to the nitro group. These results suggest that

  关于生物活性，氧化还原电势和结构效应之间可能的相关性，对几种合成的硝基芳香族化合物进行了杀虫生物测定和电化学研究（第一波还原电势的测量，Epcl）。他们中的五个表现出对光滑小球藻的显着的杀软体动物活性（LD50 <20 ppm）。Epc1值的范围为-0.532至-0.857 V（相对于Ag / AgCl（0.1 M））（-0.260至-0.585 V（相对于NHE）），均在体内降低的有利范围内。Epc1和杀软体动物活性之间的数据比较表明，电活性硝基的存在对生物活性很重要。然而，与氧化还原电位的相关性尚不明显。结构效应似乎是最重要的参数。苯酚具有更高的活性，包括对硝基偶氮或含肼的化合物。对于在硝基间位具有苄基取代基的化合物未观察到活性。这些结果表明，活性无疑涉及的不仅仅是还原特性，而且硝基还原后可能形成的亲电子物种在对光滑芽孢杆菌的杀软体动物活性中起重要作用。