(S)-2-(4-phenyl-[1,2,3]triazol-1-yl)-N4-(3-triethylsilylprop-2-ynyl)-N1-(3-triisopropylsilyl-prop-2-ynyl)-succinamide | 1189342-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-2-(4-phenyl-[1,2,3]triazol-1-yl)-N4-(3-triethylsilylprop-2-ynyl)-N1-(3-triisopropylsilyl-prop-2-ynyl)-succinamide
• 英文别名: (2S)-2-(4-phenyltriazol-1-yl)-N'-(3-triethylsilylprop-2-ynyl)-N-[3-tri(propan-2-yl)silylprop-2-ynyl]butanediamide
• CAS: 1189342-36-6
• 化学式: C₃₃H₅₁N₅O₂Si₂
• 分子量: 605.971
• InChiKey: MHJMPODFUAPCDB-HKBQPEDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  88.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-phenyl-[1,2,3]triazol-1-yl)-N4-(3-triethylsilylprop-2-ynyl)-N1-(3-triisopropylsilyl-prop-2-ynyl)-succinamide 在 水 、 silver nitrate 、 氯化铵 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (S)-2-(4-phenyl-[1,2,3]triazol-1-yl)-N4-prop-2-ynyl-N1-(3-triisopropylsilyl-prop-2-ynyl)-succinamide
  参考文献：
  名称：

  Click à la carte: robust semi-orthogonal alkyne protecting groups for multiple successive azide/alkyne cycloadditions

  摘要：

  We herein describe an in-depth screening and systematic comparison of five classical silyl alkyne protective groups, to evaluate their potential in the context of multiple successive copper (I)-catalyzed alkyne-azide cycloadditions (CuAAC). We confirm the relative sensitivity of TMS, especially under CuAAC conditions. The relative robustness of its higher analogues, and the discovery of mild silver-catalyzed deprotection conditions selective for TES compared to DPS or TIPS allowed us to design a strategy allowing three successive CuAAC on a single scaffold, as we have illustrated by the synthesis of a tris-triazolo model compound. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.093
• 作为产物：
  描述：

  (S)-2-azido-N₄-(3-triethylsilyl-prop-2-ynyl)-N₁-(3-triisopropylsilyl-prop-2-ynyl)-succinamide 、 苯乙炔 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 生成 (S)-2-(4-phenyl-[1,2,3]triazol-1-yl)-N4-(3-triethylsilylprop-2-ynyl)-N1-(3-triisopropylsilyl-prop-2-ynyl)-succinamide
  参考文献：
  名称：

  Click à la carte: robust semi-orthogonal alkyne protecting groups for multiple successive azide/alkyne cycloadditions

  摘要：

  We herein describe an in-depth screening and systematic comparison of five classical silyl alkyne protective groups, to evaluate their potential in the context of multiple successive copper (I)-catalyzed alkyne-azide cycloadditions (CuAAC). We confirm the relative sensitivity of TMS, especially under CuAAC conditions. The relative robustness of its higher analogues, and the discovery of mild silver-catalyzed deprotection conditions selective for TES compared to DPS or TIPS allowed us to design a strategy allowing three successive CuAAC on a single scaffold, as we have illustrated by the synthesis of a tris-triazolo model compound. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.093