(R)-2-(((S)-tert-butoxycarbonylamino)(2-fluorophenyl)methyl)-2-cyanocyclopentanone | 1023754-79-1

• 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)(2-fluorophenyl)methyl)-2-cyanocyclopentanone
• 英文别名: tert-butyl N-[(R)-[(1R)-1-cyano-2-oxocyclopentyl]-(2-fluorophenyl)methyl]carbamate
• CAS: 1023754-79-1
• 化学式: C₁₈H₂₁FN₂O₃
• 分子量: 332.375
• InChiKey: WRMUHPDTZCYVDI-MAUKXSAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl (NE)-N-[(2-fluorophenyl)methylidene]carbamate 、 2-氰基环戊酮 在 (S)-N-(2-hydroxyphenyl)-2-salicyloylaminoisovaleramide 、 Sc(OiPr)3 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (R)-2-(((S)-tert-butoxycarbonylamino)(2-fluorophenyl)methyl)-2-cyanocyclopentanone 、 2-((tert-butoxycarbonylamino)(2-fluorophenyl)methyl)-2-cyanocyclopentanone
  参考文献：
  名称：

  Asymmetric Catalysis via Dynamic Substrate/Ligand/Rare Earth Metal Conglomerate

  摘要：

  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.

  DOI：

  10.1021/ja800326d

文献信息

• Linking Structural Dynamics and Functional Diversity in Asymmetric Catalysis
  作者：Akihiro Nojiri、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1021/ja900084k

  日期：2009.3.18

  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.
• 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.