(4-(S)-azido-6-methyl-hept-1-ynyl)-trimethylsilane | 1204182-28-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (4-(S)-azido-6-methyl-hept-1-ynyl)-trimethylsilane
• 英文别名: [(4S)-4-azido-6-methylhept-1-ynyl]-trimethylsilane
• CAS: 1204182-28-4
• 化学式: C₁₁H₂₁N₃Si
• 分子量: 223.393
• InChiKey: PCPSMRQVERRLDW-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-(S)-azido-6-methyl-hept-1-ynyl)-trimethylsilane 、 1-[1-(1-(R)-isopropyl-but-3-ynyl)-1H-[1,2,3]triazol-4-yl]-3-phenyl-propan-2-(R)-ol 在 铜 作用下， 以 水 、 叔丁醇 为溶剂， 反应 20.5h， 以89%的产率得到(2R)-1-[1-[(2R)-3-methyl-1-[1-[(4S)-6-methyl-1-trimethylsilylhept-1-yn-4-yl]triazol-4-yl]butan-2-yl]triazol-4-yl]-3-phenylpropan-2-ol
  参考文献：
  名称：

  Synthesis of Azide-Alkyne Fragments for “Click” Chemical Applications. Part 2. Formation of Oligomers from Orthogonally Protected Chiral Trialkylsilylhomopropargyl Azides and Homopropargyl Alcohols

  摘要：

  A small library of chiral, beta(3)-substituted homopropargyl alcohols and chiral beta(3)-substituted trimethylsilylhomopropargyl azides were generated starting from natural L-amino acids. The free alkynes and azides were then coupled, using a Huisgen 1,3-dipolar cycloaddition, to provide chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as potential peptidomimetic compounds. The work is an extension to the previous synthesis of racemic, orthogonally protected 1,4-disubstituted-1,2,3-triazoles from the corresponding alpha-substituted propargyl alcohols and alpha-substituted trialkylsilylpropargyl azides.

  DOI：

  10.1021/jo9021887
• 作为产物：
  描述：

  methanesulfonic acid 1-(R)-isobutyl-4-trimethylsilanyl-but-3-ynyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以43%的产率得到(4-(S)-azido-6-methyl-hept-1-ynyl)-trimethylsilane
  参考文献：
  名称：

  Synthesis of Azide-Alkyne Fragments for “Click” Chemical Applications. Part 2. Formation of Oligomers from Orthogonally Protected Chiral Trialkylsilylhomopropargyl Azides and Homopropargyl Alcohols

  摘要：

  A small library of chiral, beta(3)-substituted homopropargyl alcohols and chiral beta(3)-substituted trimethylsilylhomopropargyl azides were generated starting from natural L-amino acids. The free alkynes and azides were then coupled, using a Huisgen 1,3-dipolar cycloaddition, to provide chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as potential peptidomimetic compounds. The work is an extension to the previous synthesis of racemic, orthogonally protected 1,4-disubstituted-1,2,3-triazoles from the corresponding alpha-substituted propargyl alcohols and alpha-substituted trialkylsilylpropargyl azides.

  DOI：

  10.1021/jo9021887

文献信息

• Synthesis of Azide-Alkyne Fragments for “Click” Chemical Applications. Part 2. Formation of Oligomers from Orthogonally Protected Chiral Trialkylsilylhomopropargyl Azides and Homopropargyl Alcohols
  作者：Oliver D. Montagnat、Guillaume Lessene、Andrew B. Hughes

  DOI：10.1021/jo9021887

  日期：2010.1.15

  A small library of chiral, beta(3)-substituted homopropargyl alcohols and chiral beta(3)-substituted trimethylsilylhomopropargyl azides were generated starting from natural L-amino acids. The free alkynes and azides were then coupled, using a Huisgen 1,3-dipolar cycloaddition, to provide chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as potential peptidomimetic compounds. The work is an extension to the previous synthesis of racemic, orthogonally protected 1,4-disubstituted-1,2,3-triazoles from the corresponding alpha-substituted propargyl alcohols and alpha-substituted trialkylsilylpropargyl azides.