(S)-3-phenyl-2-(4-((triisopropylsilyl)ethynyl)-1H-1,2,3-triazol-1-yl)propanoic acid | 1264282-98-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-3-phenyl-2-(4-((triisopropylsilyl)ethynyl)-1H-1,2,3-triazol-1-yl)propanoic acid
• 英文别名: (2S)-3-phenyl-2-[4-[2-tri(propan-2-yl)silylethynyl]triazol-1-yl]propanoic acid
• CAS: 1264282-98-5
• 化学式: C₂₂H₃₁N₃O₂Si
• 分子量: 397.593
• InChiKey: KUNPSHBYTCZNBH-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-phenyl-2-(4-((triisopropylsilyl)ethynyl)-1H-1,2,3-triazol-1-yl)propanoic acid 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.5h， 以26%的产率得到(S)-2-(4-ethynyl-1H-1,2,3-triazol-1-yl)-3-phenylpropanoic acid
  参考文献：
  名称：

  Synthesis of Unsymmetrical 1,1′-Disubstituted Bis(1,2,3-triazole)s Using Monosilylbutadiynes

  摘要：

  Bis(1,2,3-triazole)s have attracted recent interest as coordinating ligands for transition metals. Here we report a rapid, modular method for the synthesis of 1,1'-disubstituted-4,4'-linked unsymmetrical bis(1,2,3-triazole)s. The method employs sequential copper catalyzed azide-alkyne cycloaddition and deprotection steps on a monosilylbutadlyne. TMS (trimethylsilyl) and TIPS (trilsopropylsilyl) were both investigated with TIPS being the preferred protecting group due to increased stability. The reactions were amenable to one-pot synthesis, and an optimized one-pot, three-step procedure was developed.

  DOI：

  10.1021/ol102852z
• 作为产物：
  描述：

  2-methyl-6-(triisopropylsilyl)hexa-3,5-diyn-2-ol 在 copper(l) iodide 、 N,N-二异丙基乙胺 、 potassium hydroxide 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 18.5h， 生成 (S)-3-phenyl-2-(4-((triisopropylsilyl)ethynyl)-1H-1,2,3-triazol-1-yl)propanoic acid
  参考文献：
  名称：

  Synthesis of Unsymmetrical 1,1′-Disubstituted Bis(1,2,3-triazole)s Using Monosilylbutadiynes

  摘要：

  Bis(1,2,3-triazole)s have attracted recent interest as coordinating ligands for transition metals. Here we report a rapid, modular method for the synthesis of 1,1'-disubstituted-4,4'-linked unsymmetrical bis(1,2,3-triazole)s. The method employs sequential copper catalyzed azide-alkyne cycloaddition and deprotection steps on a monosilylbutadlyne. TMS (trimethylsilyl) and TIPS (trilsopropylsilyl) were both investigated with TIPS being the preferred protecting group due to increased stability. The reactions were amenable to one-pot synthesis, and an optimized one-pot, three-step procedure was developed.

  DOI：

  10.1021/ol102852z

文献信息

• Synthesis of Unsymmetrical 1,1′-Disubstituted Bis(1,2,3-triazole)s Using Monosilylbutadiynes
  作者：Bradley C. Doak、Martin J. Scanlon、Jamie S. Simpson

  DOI：10.1021/ol102852z

  日期：2011.2.4

  Bis(1,2,3-triazole)s have attracted recent interest as coordinating ligands for transition metals. Here we report a rapid, modular method for the synthesis of 1,1'-disubstituted-4,4'-linked unsymmetrical bis(1,2,3-triazole)s. The method employs sequential copper catalyzed azide-alkyne cycloaddition and deprotection steps on a monosilylbutadlyne. TMS (trimethylsilyl) and TIPS (trilsopropylsilyl) were both investigated with TIPS being the preferred protecting group due to increased stability. The reactions were amenable to one-pot synthesis, and an optimized one-pot, three-step procedure was developed.