2-(benzylideneamino)-2-(2-chlorophenyl)acetamide | 1198213-96-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(benzylideneamino)-2-(2-chlorophenyl)acetamide
• 英文别名: 2-(2-chlorophenyl)-2-[(E)-(phenylmethylidene)amino]acetamide
• CAS: 1198213-96-5
• 化学式: C₁₅H₁₃ClN₂O
• 分子量: 272.734
• InChiKey: QAPUGHQEJNBWPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzylideneamino)-2-(2-chlorophenyl)acetamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以80%的产率得到(S)-(E)-2-(benzylideneamino)-2-(2-chlorophenyl)acetamide
  参考文献：
  名称：

  Attrition-Enhanced Deracemization in the Synthesis of Clopidogrel - A Practical Application of a New Discovery

  摘要：

  The recently discovered technique of deracemization by means of attrition-induced grinding of a solid conglomerate in contact with a solution wherein racemization occurs has been used with a derivative of 2-chlorophenyl glycine, the key chiral component in the synthesis of Clopidogrel (Plavix). Deracemization of the racemate proceeds to a single enantiomer and in essentially absolute enantiomeric excess. Further conversion of enantiomerically pure material to Clopidogrel was achieved in 88% yield.

  DOI：

  10.1021/op900243c
• 作为产物：
  描述：

  2-氨基-2-(2-氯苯基)乙酸甲酯 在 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 2-(benzylideneamino)-2-(2-chlorophenyl)acetamide
  参考文献：
  名称：

  Pasteur’s Tweezers Revisited: On the Mechanism of Attrition-Enhanced Deracemization and Resolution of Chiral Conglomerate Solids

  摘要：

  Insights into the mechanism of attrition-enhanced deracemization and resolution of solid enantiomorphic chiral compounds are obtained by crystal size and solubility measurements and by isotopic labeling experiments. Together these results help to deconvolute the various chemical and physical rate processes contributing to the phenomenon. Crystal size measurements highlight a distinct correlation between the stochastic, transient growth of crystals and the emergence of a single solid enantiomorph under attrition conditions. The rapid mass transfer of molecules between the solution and solid phases under attrition is demonstrated, and the concept of a crystal-size-induced solubility driving force is exploited to overcome the stochastic nature of the crystal growth and dissolution processes. Extension to non-racemizing conditions provides a novel methodology for chiral resolution. Implications both for practical chiral separations and for the origin of biological homochirality are discussed.

  DOI：

  10.1021/ja303566g

文献信息

• Isotopically Directed Symmetry Breaking and Enantioenrichment in Attrition-Enhanced Deracemization
  作者：James I. Murray、Jacob N. Sanders、Paul F. Richardson、K. N. Houk、Donna G. Blackmond

  DOI：10.1021/jacs.9b11422

  日期：2020.2.26

  The evolution of homochirality via attrition-enhanced deracemization (AED) of enantiomorphic solids is carried out using molecules that differ only in the isotopic composition of a phenyl group positioned remote from the chiral center. Enantioenrichment consistently favors the enantiomorph containing a deuterated phenyl group over the protio or C-13 version, and the protio version is consistently favored over the C-13 version. While these isotopic compounds exhibit identical crystal structures and solubilities, the trend in deracemization correlates with melting points. Understanding the origin of this isotope bias provides fundamental clues about overcoming stochastic behavior to direct the stereochemical outcome in attrition-enhanced deracemization processes. The energy required for breaking symmetry with chiral bias is compared for this near-equilibrium AED process and the far-from-equilibrium Soai autocatalytic reaction. Implications for the origin of biological homochirality are discussed.
• Scaling Up Attrition-Enhanced Deracemization by Use of an Industrial Bead Mill in a Route to Clopidogrel (Plavix)
  作者：W. L. Noorduin、P. van der Asdonk、A. A. C. Bode、H. Meekes、W. J. P. van Enckevort、E. Vlieg、B. Kaptein、M. W. van der Meijden、R. M. Kellogg、G. Deroover

  DOI：10.1021/op1001116

  日期：2010.7.16

  The recently discovered technique of deracemization by means of grinding a racemic conglomerate in contact with a solution wherein racemization occurs has been scaled up using an industrial bead mill to demonstrate the practical applicability. The time needed to reach the enantiopure end state is drastically reduced as a mull of the efficient grinding that can be achieved using head mills.