(2R)-1-[1-[(2R)-3-methyl-1-[1-[(4S)-6-methylhept-1-yn-4-yl]triazol-4-yl]butan-2-yl]triazol-4-yl]-3-phenylpropan-2-ol | 1204182-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-1-[1-[(2R)-3-methyl-1-[1-[(4S)-6-methylhept-1-yn-4-yl]triazol-4-yl]butan-2-yl]triazol-4-yl]-3-phenylpropan-2-ol
• CAS: 1204182-94-4
• 化学式: C₂₆H₃₆N₆O
• 分子量: 448.611
• InChiKey: SENPXGPMIXXTQS-TWJOJJKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(R)-azido-7-trimethylsilanyl-hept-6-ynoic acid methyl ester 、 (2R)-1-[1-[(2R)-3-methyl-1-[1-[(4S)-6-methylhept-1-yn-4-yl]triazol-4-yl]butan-2-yl]triazol-4-yl]-3-phenylpropan-2-ol 在 铜 作用下， 以 水 、 叔丁醇 为溶剂， 反应 20.5h， 以80%的产率得到4-{4-[2-(4-{2-[4-(2-(R)-hydroxy-3-phenyl-propyl)-(R)-[1,2,3]triazol-1-yl]-3-methylbutyl}-(S)-[1,2,3]triazol-1-yl)-4-methyl-pentyl]-(R)-[1,2,3]triazol-1-yl}-7-trimethylsilanyl-hept-6-ynoic acid methyl 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：

  (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 在 甲醇 、 potassium carbonate 作用下， 反应 0.5h， 以94%的产率得到(2R)-1-[1-[(2R)-3-methyl-1-[1-[(4S)-6-methylhept-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