1-pentafluorophenyl-4-phenyl-1H-[1,2,3]triazole | 53887-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-pentafluorophenyl-4-phenyl-1H-[1,2,3]triazole
• 英文别名: 1-Pentafluor-4-phenyl-1,2,3-triazol
• CAS: 53887-79-9
• 化学式: C₁₄H₆F₅N₃
• 分子量: 311.214
• InChiKey: RTCCKESYPZINOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-pentafluorophenyl-4-phenyl-1H-[1,2,3]triazole 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 碘 作用下， 以 四氢呋喃 为溶剂， 以57 %的产率得到5-iodo-1-(perfluorophenyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Lithiation‐Functionalisation of Triazoles Bearing Electron‐Withdrawing N ‐Substituents: Challenges and Solutions**

  摘要：

  AbstractThe regioselective lithiation of 1,2,3‐triazoles provides an opportunity to introduce additional functionality, however this simple functionalisation strategy using triazoles bearing electron‐withdrawing N‐substituents has not been investigated until now. Herein, we demonstrate that the lithiated triazole intermediates can readily decompose, even at −78 °C. In addition, lithiation‐deuteration studies reveal lithiation can take place competitively on both the triazole and the electron‐withdrawn aryl ring. Careful control of reaction conditions is therefore required to i) minimise decomposition pathways; and ii) facilitate regioselective functionalisation of the triazole.

  DOI：

  10.1002/ejoc.202201459
• 作为产物：
  描述：

  perfluorophenyl azide 、 苯乙炔 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 二氯甲烷 为溶剂， 以90 %的产率得到1-pentafluorophenyl-4-phenyl-1H-[1,2,3]triazole
  参考文献：
  名称：

  Lithiation‐Functionalisation of Triazoles Bearing Electron‐Withdrawing N ‐Substituents: Challenges and Solutions**

  摘要：

  AbstractThe regioselective lithiation of 1,2,3‐triazoles provides an opportunity to introduce additional functionality, however this simple functionalisation strategy using triazoles bearing electron‐withdrawing N‐substituents has not been investigated until now. Herein, we demonstrate that the lithiated triazole intermediates can readily decompose, even at −78 °C. In addition, lithiation‐deuteration studies reveal lithiation can take place competitively on both the triazole and the electron‐withdrawn aryl ring. Careful control of reaction conditions is therefore required to i) minimise decomposition pathways; and ii) facilitate regioselective functionalisation of the triazole.

  DOI：

  10.1002/ejoc.202201459

文献信息

• <i>N</i>,<i>N</i>-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes
  作者：Sheng Xie、Olof Ramström、Mingdi Yan

  DOI：10.1021/ol503655a

  日期：2015.2.6

  Experimental data support 1,3-dipolar cycloaddition between DEU-activated enols and electrophilic phenyl azides, especially perfluoroaryl azides, followed by rearrangement of the triazoline intermediate. The activation of the aldehyde under near-neutral conditions was of special importance in inhibiting dehydration/aromatization of the triazoline intermediate, thus promoting the rearrangement to form aryl amides

  脲结构，其中Ñ，Ñ证明-diethylurea（德国）是最有效的，被发现对缺电子的芳基叠氮化物和phenylacetaldehydes之间催化酰胺化反应。实验数据支持DEU活化的烯醇与亲电子的苯基叠氮化物（尤其是全氟芳基叠氮化物）之间的1,3-偶极环加成反应，然后重排三唑啉中间体。在接近中性的条件下，醛的活化在抑制三唑啉中间体的脱水/芳构化，从而促进重排形成芳基酰胺方面特别重要。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.8, 3, page 55 - 151
  作者：

  DOI：——

  日期：——
• Banks, R. E.; Prakash, A., Journal of the Chemical Society. Perkin transactions I, 1974, p. 1365 - 1371
  作者：Banks, R. E.、Prakash, A.

  DOI：——

  日期：——
• New reactions of azidopentafluorobenzene; intermolecular ′insertions′ into n-h bonds
  作者：R.E. Banks、A. Prakash

  DOI：10.1016/s0040-4039(01)95587-x

  日期：1973.1