4-ethyl-1-(4-nitrophenyl)-1H-1,2,3-triazole | 1276538-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-ethyl-1-(4-nitrophenyl)-1H-1,2,3-triazole
• 英文别名: 4-ethyl-1-(4-nitrophenyl)triazole
• CAS: 1276538-19-2
• 化学式: C₁₀H₁₀N₄O₂
• 分子量: 218.215
• InChiKey: NSFJULHTFQSZNS-UHFFFAOYSA-N

物化性质

• 熔点：
  144-145 °C(Solv: toluene (108-88-3))
• 沸点：
  396.5±44.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-硝基碘苯 、 2-戊炔酸 在 sodium azide 、 potassium carbonate 、 L-脯氨酸 、 copper(l) chloride 作用下， 以 二甲基亚砜 为溶剂， 以75%的产率得到4-ethyl-1-(4-nitrophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Tandem Catalysis: From Alkynoic Acids and Aryl Iodides to 1,2,3-Triazoles in One Pot

  摘要：

  A tandem catalysis protocol based on decarboxylative coupling of alkynoic acids and 1,3-dipolar cycloaddition of azides enables a highly efficient synthesis of a variety of functionalized 1,2,3-triazoles. The three-step, one-pot method avoids usage of gaseous or highly volatile terminal alkynes, reduces handling of potentially unstable and explosive azides to a minimum, and furnishes target structures in excellent yields and a very good purity without the need for additional purification.

  DOI：

  10.1021/jo1024927

文献信息

• An Organocatalytic Azide-Aldehyde [3+2] Cycloaddition: High-Yielding Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
  作者：Dhevalapally B. Ramachary、Adluri B. Shashank、S. Karthik

  DOI：10.1002/anie.201406721

  日期：2014.9.22

  An organocatalytic azide–aldehyde [3+2] cycloaddition (organo‐click) reaction of a variety of enolizable aldehydes is reported. The organo‐click reaction is characterized by a high rate and regioselectivity, mild reaction conditions, easily available substrates with simple operation, and excellent yields with a broad spectrum of substrates. It constitutes an alternative to the previously known CuAAC

  报道了多种可烯化醛的有机催化叠氮化物-醛[3 + 2]环加成（有机点击）反应。有机点击反应的特点是高速率和区域选择性，温和的反应条件，易于获得的底物和简单的操作，以及具有广泛底物范围的优异收率。它构成了以前已知的CuAAC，RuAAC和IrAAC点击反应的替代方法。
• Tandem Catalysis: From Alkynoic Acids and Aryl Iodides to 1,2,3-Triazoles in One Pot
  作者：Andrej Kolarovič、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1021/jo1024927

  日期：2011.4.15

  A tandem catalysis protocol based on decarboxylative coupling of alkynoic acids and 1,3-dipolar cycloaddition of azides enables a highly efficient synthesis of a variety of functionalized 1,2,3-triazoles. The three-step, one-pot method avoids usage of gaseous or highly volatile terminal alkynes, reduces handling of potentially unstable and explosive azides to a minimum, and furnishes target structures in excellent yields and a very good purity without the need for additional purification.