(S)-N-(2-(benzyloxy)phenyl)-2-(2-(2-hydroxyphenyl)acetamido)-3-methylbutanamide | 1231929-56-8

• 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: (S)-N-(2-(benzyloxy)phenyl)-2-(2-(2-hydroxyphenyl)acetamido)-3-methylbutanamide
• CAS: 1231929-56-8
• 化学式: C₂₆H₂₈N₂O₄
• 分子量: 432.519
• InChiKey: YBKXVBNRIFWJCA-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  87.66
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(2-(benzyloxy)phenyl)-2-(2-(2-hydroxyphenyl)acetamido)-3-methylbutanamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 以99%的产率得到(S)-N-(2-hydroxyphenyl)-2-(2-(2-hydroxyphenyl)acetamido)-3-methylbutanamide
  参考文献：
  名称：

  Solvent-Dependent Self-Discrimination of Bis(2-hydroxyphenyl)diamides

  摘要：

  AbstractSolvent‐dependent, self‐discrimination of diamides is described. Mixing a solution of (R)‐1 a and (S)‐1 a, which are valine‐derived, bis(2‐hydroxyphenyl)diamide‐bearing, multiple hydrogen‐bonding modules, in dichloromethane immediately led to the formation of a thick suspension comprising a 1:1 heterochiral aggregate of 1 a. The solubility of heterochiral 1 a was substantially lower in halogenated solvents than in ethyl acetate. A perusal of racemic crystal structures obtained from chloroform and ethyl acetate revealed a significant difference in the crystal‐packing pattern, which is likely to be the basis for the pronounced difference in solubility. Specific self‐discrimination of 1 a in an ensemble of eight structurally related molecules showcased the specific aggregation through the hydrogen‐bonding network of the bis(2‐hydroxyphenyl)diamide framework. The low solubility of heterochiral 1 a in halogenated solvent was exploited to achieve high stereoselectivity in a catalytic asymmetric reaction by using a low enantiomeric excess sample of 1 a.

  DOI：

  10.1002/chem.201000321
• 作为产物：
  描述：

  苯并呋喃-2(3H)-酮 、 (S)-2-amino-N-(2-(benzyloxy)phenyl)-3-methylbutanamide 以 甲苯 为溶剂， 反应 2.5h， 以1.49 g的产率得到(S)-N-(2-(benzyloxy)phenyl)-2-(2-(2-hydroxyphenyl)acetamido)-3-methylbutanamide
  参考文献：
  名称：

  Solvent-Dependent Self-Discrimination of Bis(2-hydroxyphenyl)diamides

  摘要：

  AbstractSolvent‐dependent, self‐discrimination of diamides is described. Mixing a solution of (R)‐1 a and (S)‐1 a, which are valine‐derived, bis(2‐hydroxyphenyl)diamide‐bearing, multiple hydrogen‐bonding modules, in dichloromethane immediately led to the formation of a thick suspension comprising a 1:1 heterochiral aggregate of 1 a. The solubility of heterochiral 1 a was substantially lower in halogenated solvents than in ethyl acetate. A perusal of racemic crystal structures obtained from chloroform and ethyl acetate revealed a significant difference in the crystal‐packing pattern, which is likely to be the basis for the pronounced difference in solubility. Specific self‐discrimination of 1 a in an ensemble of eight structurally related molecules showcased the specific aggregation through the hydrogen‐bonding network of the bis(2‐hydroxyphenyl)diamide framework. The low solubility of heterochiral 1 a in halogenated solvent was exploited to achieve high stereoselectivity in a catalytic asymmetric reaction by using a low enantiomeric excess sample of 1 a.

  DOI：

  10.1002/chem.201000321