2,4,6-triazido-3,5-difluoropyridine | 258843-16-2

• 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: 2,4,6-triazido-3,5-difluoropyridine
• CAS: 258843-16-2
• 化学式: C₅F₂N₁₀
• 分子量: 238.119
• InChiKey: AFARKDSJCGZSCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,4,6-triazido-3,5-difluoropyridine 生成 3,5-difluoropyridyl-2,4,6-trinitrene 、 4-azido-3,5-difluoropyridyl-2,6-dinitrene 、 2-azido-3,5-difluoropyridyl-4,6-dinitrene 、 2,6-diazido-3,5-difluoropyridyl-4-nitrene 、 2,4-diazido-3,5-difluoropyridyl-6-nitrene
  参考文献：
  名称：

  Matrix Isolation and EPR Spectroscopy of Septet 3,5-Difluoropyridyl-2,4,6-trinitrene

  摘要：

  Septet 3,5-difluoropyridlyl-2,4,6-dinitrene along with quintet 2-azido-3,5-difluoropyridyl-4,6-dinitrene, quintet 4-azido-3,5-difluoropyridyl-2,6-dinitrene, triplet 2,6-diazido-3,5-difluoropyridyl-4-nitrene, and triplet 2,4-diazido-3,5-difluoropyridyl-6-nitrene have been obtained by photolysis of 2,4,6-triazido-3,5-difluoropyridine in solid argon at 4 K. The electronic and magnetic properties of the matrix-isolated nitrenes were studied using electron paramagnetic resonance (EPR) spectroscopy in combination with density functional theory (DFT) calculations. The fine-structure parameters of the nitrenes were determined with high accuracy from computer spectral simulations. All signals in the EPR spectra of the nitrenes randomly oriented in the solid phase were unambiguously assigned on the basis of eigenfield calculations of the Zeeman energy levels and angular dependencies of resonance fields from the direction of the applied magnetic field.

  DOI：

  10.1021/jo800425k
• 作为产物：
  描述：

  五氟吡啶 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 以96%的产率得到2,4,6-triazido-3,5-difluoropyridine
  参考文献：
  名称：

  Di- and triazidation of 3-chlorotetrafluoropyridine

  摘要：

  3-Chlorotetrafluoropyridine and pentafluoropyridine readily react with an excess of sodium azide in dimethylsulfoxide at room temperature to give corresponding 2.4,6-triazido-3-chloro-5-fluoropyridine and 2,4,6-triazido-3,5-difluoropyridine in high yields. The reaction of asymmetric 3-chlorotetrafluorpyridine with two equimolar amounts of sodium azide under similar reaction conditions occurs regioselectively to give 2,4-diazido-5-chloro-3,6-difluoropyridine as a sole product. (19)F, (13)C and (15)N NMR spectral characteristics of the triazides suggest that these compounds can be of interest as cross-linking reagents for polymer chemistry and as starting materials for organic synthesis. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.07.012

文献信息

• Synthesis of 2,4,6-triazido-3,5-difluoropyridine
  作者：S. V. Chapyshev

  DOI：10.1007/bf02324653

  日期：1999.5
• ——
  作者：S. V. Chapyshev

  DOI：10.1023/a:1012783416802

  日期：——
• Di- and triazidation of 3-chlorotetrafluoropyridine
  作者：Sergei V. Chapyshev

  DOI：10.1016/j.jfluchem.2011.07.012

  日期：2011.11

  3-Chlorotetrafluoropyridine and pentafluoropyridine readily react with an excess of sodium azide in dimethylsulfoxide at room temperature to give corresponding 2.4,6-triazido-3-chloro-5-fluoropyridine and 2,4,6-triazido-3,5-difluoropyridine in high yields. The reaction of asymmetric 3-chlorotetrafluorpyridine with two equimolar amounts of sodium azide under similar reaction conditions occurs regioselectively to give 2,4-diazido-5-chloro-3,6-difluoropyridine as a sole product. (19)F, (13)C and (15)N NMR spectral characteristics of the triazides suggest that these compounds can be of interest as cross-linking reagents for polymer chemistry and as starting materials for organic synthesis. (C) 2011 Elsevier B.V. All rights reserved.
• Matrix Isolation and EPR Spectroscopy of Septet 3,5-Difluoropyridyl-2,4,6-trinitrene
  作者：Sergei V. Chapyshev、Dirk Grote、Christopher Finke、Wolfram Sander

  DOI：10.1021/jo800425k

  日期：2008.9.19

  Septet 3,5-difluoropyridlyl-2,4,6-dinitrene along with quintet 2-azido-3,5-difluoropyridyl-4,6-dinitrene, quintet 4-azido-3,5-difluoropyridyl-2,6-dinitrene, triplet 2,6-diazido-3,5-difluoropyridyl-4-nitrene, and triplet 2,4-diazido-3,5-difluoropyridyl-6-nitrene have been obtained by photolysis of 2,4,6-triazido-3,5-difluoropyridine in solid argon at 4 K. The electronic and magnetic properties of the matrix-isolated nitrenes were studied using electron paramagnetic resonance (EPR) spectroscopy in combination with density functional theory (DFT) calculations. The fine-structure parameters of the nitrenes were determined with high accuracy from computer spectral simulations. All signals in the EPR spectra of the nitrenes randomly oriented in the solid phase were unambiguously assigned on the basis of eigenfield calculations of the Zeeman energy levels and angular dependencies of resonance fields from the direction of the applied magnetic field.