(S)-N-(2-hydroxyphenyl)-2-(benzoylamino)isovaleramide | 1231929-49-9

• 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: (S)-N-(2-hydroxyphenyl)-2-(benzoylamino)isovaleramide
• CAS: 1231929-49-9
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: MWUVQFGHZNJFIH-INIZCTEOSA-N

反应信息

• 作为产物：
  描述：

  (S)-N-(2-benzyloxyphenyl)-2-(benzoylamino)isovaleramide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 以91%的产率得到(S)-N-(2-hydroxyphenyl)-2-(benzoylamino)isovaleramide
  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