(S)-2-(((S)-tert-butoxycarbonylamino)(3-thienyl)methyl)-2-cyanocyclopentanone | 1123681-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (S)-2-(((S)-tert-butoxycarbonylamino)(3-thienyl)methyl)-2-cyanocyclopentanone
• CAS: 1123681-85-5
• 化学式: C₁₆H₂₀N₂O₃S
• 分子量: 320.412
• InChiKey: JPWUCENYZIZASX-BBRMVZONSA-N

物化性质

• 沸点：
  519.8±50.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.19
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  tert-butyl thiophen-3-ylmethylenecarbamate 、 2-氰基环戊酮 在 erbium triisopropoxide 、 (S)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以99%的产率得到(S)-2-(((S)-tert-butoxycarbonylamino)(3-thienyl)methyl)-2-cyanocyclopentanone
  参考文献：
  名称：

  Linking Structural Dynamics and Functional Diversity in Asymmetric Catalysis

  摘要：

  Proteins, the functional molecules in biological systems, are sophisticated chemical devices that have evolved over billions of years. Their function is intimately related to their three-dimensional structure and elegantly regulated by conformational changes through allosteric regulators and a number of reversible or unidirectional post-translational modifications. This functional diversification in response to external stimuli allows for an orderly and timely progression of intra- and extracellular events. In contrast, enantioselective catalysts generally exhibit limited conformational flexibility and thereby exert a single specific function. Exploiting the features of conformationally flexible asymmetric ligands and the variable coordination patterns of rare earth metals, we demonstrate dynamic structural and functional changes of a catalyst in asymmetric catalysis, leading to two distinct reaction outcomes in a single flask.

  DOI：

  10.1021/ja900084k