6-methyl-1-trimethylsilanyl-hept-1-yn-4-(R)-ol | 1204181-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-methyl-1-trimethylsilanyl-hept-1-yn-4-(R)-ol
• 英文别名: (4R)-6-methyl-1-trimethylsilylhept-1-yn-4-ol
• CAS: 1204181-83-8
• 化学式: C₁₁H₂₂OSi
• 分子量: 198.381
• InChiKey: YWNHTAAPMNNVHC-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-methyl-1-trimethylsilanyl-hept-1-yn-4-(R)-ol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到methanesulfonic acid 1-(R)-isobutyl-4-trimethylsilanyl-but-3-ynyl ester
  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：

  (R)-2-isobutyloxirane 、 三甲基乙炔基硅 在 正丁基锂 、 三氟化硼乙醚 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以59%的产率得到6-methyl-1-trimethylsilanyl-hept-1-yn-4-(R)-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

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.