methanesulfonic acid 1-(S)-isopropyl-4-trimethylsilanyl-but-3-ynyl ester | 1204182-01-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: methanesulfonic acid 1-(S)-isopropyl-4-trimethylsilanyl-but-3-ynyl ester
• 英文别名: [(3S)-2-methyl-6-trimethylsilylhex-5-yn-3-yl] methanesulfonate
• CAS: 1204182-01-3
• 化学式: C₁₁H₂₂O₃SSi
• 分子量: 262.445
• InChiKey: DUWDZIPSHICJTD-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  16
• 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：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 1-(S)-isopropyl-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44%的产率得到(4-(R)-azido-5-methyl-hex-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
• 作为产物：
  描述：

  甲基磺酰氯 、 2-methyl-6-trimethylsilanyl-hex-5-yn-3-(S)-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到methanesulfonic acid 1-(S)-isopropyl-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

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.