N-(2-methylbenzylidine)phenylglycine amide | 1006656-85-4

• 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: N-(2-methylbenzylidine)phenylglycine amide
• 英文别名: N-(2-methylbenzylidine) phenylglycin amide；N-(2-methylbenzylidene)-phenylglycine amide；2-[(2-Methylphenyl)methylideneamino]-2-phenylacetamide
• CAS: 1006656-85-4
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: UJHJTLWIYKUKKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  N-(2-methylbenzylidine)phenylglycine amide 在 左旋苯甘氨酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 (2S)-N-(2-methylbenzylidine)phenylglycine amide
  参考文献：
  名称：

  对映选择性对称性破坏受制于工艺步骤的顺序

  摘要：

  反向进行：可以简单地通过组合不同反应混合物成分的顺序（参见方案I），玻璃珠，II）外消旋混合物（对映体由颜色），III）溶剂，IV）外消旋催化剂）。潜在的机理基于对映选择性晶体生长和溶解之间的微妙平衡。

  DOI：

  10.1002/anie.200907231
• 作为产物：
  描述：

  (2S)-N-(2-methylbenzylidine)phenylglycine amide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 生成 N-(2-methylbenzylidine)phenylglycine amide
  参考文献：
  名称：

  Linear Deracemization Kinetics during Viedma Ripening: Autocatalysis Overruled by Chiral Additives

  摘要：

  Viedma ripening proceeds through an autocatalytic feedback mechanism which exponentially deracemizes an initially racemic solid state to an enantiopure end state. Here we show that, in the presence of enantiopure additives with a concentration of as low as 2.5 × 10–2 mol %, Viedma ripening proceeds with an overall linear and faster increase in enantiomeric excess. These experimental results can be explained using a simple model which assumes a difference in growth and dissolution rates between the enantiomers. This model also accounts for the generally observed linearity during the initial stages of Viedma ripening without additives.

  DOI：

  10.1021/acs.cgd.5b00127

文献信息

• Complete Deracemization by Attrition-Enhanced Ostwald Ripening Elucidated
  作者：Wim L. Noorduin、Hugo Meekes、Willem J. P. van Enckevort、Alessia Millemaggi、Michel Leeman、Bernard Kaptein、Richard M. Kellogg、Elias Vlieg

  DOI：10.1002/anie.200801846

  日期：2008.8.11
• Controlling the Effect of Chiral Impurities on Viedma Ripening
  作者：René R. E. Steendam、Bram Harmsen、Hugo Meekes、Willem J. P. van Enckevort、Bernard Kaptein、Richard M. Kellogg、Jan Raap、Floris P. J. T. Rutjes、Elias Vlieg

  DOI：10.1021/cg400927m

  日期：2013.11.6

  Spontaneous symmetry breaking and chiral amplification by means of Viedma ripening by definition should result in complete deracemization of a racemic conglomerate into either one of the enantiomers with equal probability. In practice, however, chiral impurities influence Viedma ripening and one enantiomer is obtained in preference over the other. Here, we show that by increasing the attrition intensity during Viedma ripening, the effect of chiral impurities is suppressed and deracemization does yield either enantiomer with equal probability. The reason for this is that the resulting smaller crystals lead to such a low surface density of chiral impurities that they no longer inhibit the crystal growth sufficiently to determine the chiral outcome. Furthermore, we show that even for low attrition intensities, the effect of chiral impurities can be canceled by using the right amount (10 ppm) of chiral additives.
• Attrition-enhanced total resolution leads to homochiral families of amino acid derivatives
  作者：Michel Leeman、Jesse M. de Gooier、Karin Boer、Karen Zwaagstra、Bernard Kaptein、Richard M. Kellogg

  DOI：10.1016/j.tetasy.2010.04.007

  日期：2010.5

  The total resolution of five structurally similar racemizable amino acid derivatives, three of which have racemic crystal structures, was performed simultaneously. By enantioselective incorporation in an amino acid derivative that forms a conglomerate the other four were deracemized on attrition-induced grinding. The outcome of the resolution was random (R) or (S), but all compounds had the same absolute configuration and high enantiomeric purities. (C) 2010 Published by Elsevier Ltd.