1-((triisopropylsilyl)ethynyl)-1H-indazole | 1206196-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 1-((triisopropylsilyl)ethynyl)-1H-indazole
• 英文别名: 2-Indazol-1-ylethynyl-tri(propan-2-yl)silane
• CAS: 1206196-88-4
• 化学式: C₁₈H₂₆N₂Si
• 分子量: 298.503
• InChiKey: IJCBKUAOYQQBDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-((triisopropylsilyl)ethynyl)-1H-indazole 在 copper(ll) sulfate pentahydrate 、 sodium L-ascorbate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.5h， 生成 1-(1-Benzyltriazol-4-yl)indazole
  参考文献：
  名称：

  Triazoles from N-Alkynylheterocycles and Their Coordination to Iridium

  摘要：

  N-alkynylheterocycles (benzimidazole and indazole) are converted to triazoles by click chemistry, and the resulting triazoles react with [IrCl2Cp*](2). The benzimidazole-triazole coordinates in a monodentate fashion through the benzimidazole, whereas the indazole-triazole is bidentate through coordination of both heterocycles. Reaction of the benzimidazole-triazole with methyliodide gives a benzimidazolium salt that deprotonates on coordination to afford a rare example of a bidentate NHC-triazole.

  DOI：

  10.1021/om201157g
• 作为产物：
  描述：

  吲唑 、 (2-溴乙炔基)三异丙基硅烷 在 copper(l) iodide 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以83%的产率得到1-((triisopropylsilyl)ethynyl)-1H-indazole
  参考文献：
  名称：

  Cu-Catalyzed N-Alkynylation of Imidazoles, Benzimidazoles, Indazoles, and Pyrazoles Using PEG as Solvent Medium

  摘要：

  A facile and efficient Cu(I)-catalyzed cross-coupling method is reported for the preparation of N-alkynyl or N-bromoalkenyl heteroarenes from bromoalkynes. Generally superior yields and functional group tolerance were obtained with microwave (MW) irradiation using imidazole, benzimidazole, pyrazole, and indazole substrates and poly(ethylene glycol) 400 (PEG400) as an additive. We speculate that PEG400 acts as both a Cu(I)-stabilizing ligand as well as a phase transfer solvent.

  DOI：

  10.1021/jo902466f

文献信息

• Cu-Catalyzed N<i>-</i>Alkynylation of Imidazoles, Benzimidazoles, Indazoles, and Pyrazoles Using PEG as Solvent Medium
  作者：Glenn A. Burley、David L. Davies、Gerry A. Griffith、Michael Lee、Kuldip Singh

  DOI：10.1021/jo902466f

  日期：2010.2.5

  A facile and efficient Cu(I)-catalyzed cross-coupling method is reported for the preparation of N-alkynyl or N-bromoalkenyl heteroarenes from bromoalkynes. Generally superior yields and functional group tolerance were obtained with microwave (MW) irradiation using imidazole, benzimidazole, pyrazole, and indazole substrates and poly(ethylene glycol) 400 (PEG400) as an additive. We speculate that PEG400 acts as both a Cu(I)-stabilizing ligand as well as a phase transfer solvent.
• Triazoles from N-Alkynylheterocycles and Their Coordination to Iridium
  作者：Glenn A. Burley、Youcef Boutadla、David L. Davies、Kuldip Singh

  DOI：10.1021/om201157g

  日期：2012.2.13

  N-alkynylheterocycles (benzimidazole and indazole) are converted to triazoles by click chemistry, and the resulting triazoles react with [IrCl2Cp*](2). The benzimidazole-triazole coordinates in a monodentate fashion through the benzimidazole, whereas the indazole-triazole is bidentate through coordination of both heterocycles. Reaction of the benzimidazole-triazole with methyliodide gives a benzimidazolium salt that deprotonates on coordination to afford a rare example of a bidentate NHC-triazole.