(R)-2-((S)-tert-butoxycarbonylamino)benzyl-2-cyanocyclohexanone | 1023754-72-4

• 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: (R)-2-((S)-tert-butoxycarbonylamino)benzyl-2-cyanocyclohexanone
• 英文别名: tert-butyl N-[(S)-[(1R)-1-cyano-2-oxocyclohexyl]-phenylmethyl]carbamate
• CAS: 1023754-72-4
• 化学式: C₁₉H₂₄N₂O₃
• 分子量: 328.411
• InChiKey: PZYQACNQBOYQKU-QFBILLFUSA-N

物化性质

• 熔点：
  48-49 °C
• 沸点：
  515.3±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氧代环己烷甲腈 、 benzaldehyde N-boc imine 在 erbium triisopropoxide 、 (S)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 (R)-2-((S)-tert-butoxycarbonylamino)benzyl-2-cyanocyclohexanone 、 (S)-2-((S)-tert-butoxycarbonylamino)benzyl-2-cyanocyclohexanone
  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

文献信息

• Asymmetric Catalysis via Dynamic Substrate/Ligand/Rare Earth Metal Conglomerate
  作者：Akihiro Nojiri、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1021/ja800326d

  日期：2008.4.1

  A highly enantio- and diastereoselective catalytic asymmetric Mannich-type reaction of acyanoketones and N-Boc imines promoted by an amide ligand/Sc(OiPr)(3) catalyst is described. The similar reaction outcome is obtained with/without precomplexation of catalyst, suggesting that reaction i components in a non-ordered conglomerate mixture orchestrate to form an ordered transition state during the reaction. Spectroscopic data and Eyring plot are consistent with this assumption.