2-azido-5-formylbenzonitrile | 1193501-29-9

• 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: 2-azido-5-formylbenzonitrile
• CAS: 1193501-29-9
• 化学式: C₈H₄N₄O
• 分子量: 172.146
• InChiKey: VKIZCQPXJYVBPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azido-5-formylbenzonitrile 、 2-(3-氰基-4,5,5-三甲基呋喃-2(5H)-亚甲基)丙二腈 在 ammonium acetate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 16.0h， 生成 2-(4-(4-amino-3-cyanostyryl)-3-cyano-5,5-dimethylfuran-2(5H)-ylidene)malononitrile
  参考文献：
  名称：

  Azido Push−Pull Fluorogens Photoactivate to Produce Bright Fluorescent Labels

  摘要：

  Dark azido push-pull chromophores have the ability to be photoactivated to produce bright fluorescent labels suitable for single-molecule imaging Upon illumination, the aryl azide functionality in the fluorogens participates in a photochemical conversion to an aryl amine thus restoring charge-transfer absorption and fluorescence Previously we reported that one compound DCDHF-V-P-azide was photoactivatable Here we demonstrate that the azide-to amine photoactivation process is generally applicable to a variety of push-pull chromophores, and we characterize the photophysical parameters including photoconversion quantum yield photostability and turn-on ratio Azido push-pull fluorogens provide a new class of photoactivatable single molecule probes for flourescent labeling and super-resolution microscopy Lastly we demonstrate that photoactivated push-pull dyes can insert into bonds of nearby biomolecules, simultaneously forming a covalent bond and becoming fluorescent (fluorogenic photoaffinity labeling)

  DOI：

  10.1021/jp907080r
• 作为产物：
  描述：

  3-溴-4-氟苯甲醛 在 sodium azide 作用下， 以 N-甲基吡咯烷酮 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 2-azido-5-formylbenzonitrile
  参考文献：
  名称：

  Azido Push−Pull Fluorogens Photoactivate to Produce Bright Fluorescent Labels

  摘要：

  Dark azido push-pull chromophores have the ability to be photoactivated to produce bright fluorescent labels suitable for single-molecule imaging Upon illumination, the aryl azide functionality in the fluorogens participates in a photochemical conversion to an aryl amine thus restoring charge-transfer absorption and fluorescence Previously we reported that one compound DCDHF-V-P-azide was photoactivatable Here we demonstrate that the azide-to amine photoactivation process is generally applicable to a variety of push-pull chromophores, and we characterize the photophysical parameters including photoconversion quantum yield photostability and turn-on ratio Azido push-pull fluorogens provide a new class of photoactivatable single molecule probes for flourescent labeling and super-resolution microscopy Lastly we demonstrate that photoactivated push-pull dyes can insert into bonds of nearby biomolecules, simultaneously forming a covalent bond and becoming fluorescent (fluorogenic photoaffinity labeling)

  DOI：

  10.1021/jp907080r

文献信息

• Synthesis of azido-substituted benzaldehydes via S Ar chemistry
  作者：Arjun Kafle、Sandy Yossef、Scott T. Handy

  DOI：10.1016/j.tetlet.2020.151899

  日期：2020.5

  Conditions for the formation of azidobenzaldehydes and azidobenzonitriles using sodium azide in DMSO under typical SNAr conditions are described. This simplifies access to these valuable building blocks compared to the more common sequences reported in the literature. Interestingly, fluorosubstituted aryl ketones and esters do not afford azides, but instead amine products.

  用于使用在DMSO中的叠氮化钠典型的S下azidobenzaldehydes和azidobenzonitriles形成的条件Ñ氩条件描述。与文献中报道的更常见的序列相比，这简化了对这些有价值的构建基块的访问。有趣的是，氟取代的芳基酮和酯不提供叠氮化物，而是胺产物。