N-<(2-Hydroxy-1-naphthyl)methylene>-(S)-phenylglycine cyclohexylamide | 136604-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-<(2-Hydroxy-1-naphthyl)methylene>-(S)-phenylglycine cyclohexylamide
• 英文别名: (2S)-N-cyclohexyl-2-[(2-hydroxynaphthalen-1-yl)methylideneamino]-2-phenylacetamide
• CAS: 136604-27-8
• 化学式: C₂₅H₂₆N₂O₂
• 分子量: 386.494
• InChiKey: JJVBMPUHVBUWTN-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-Phgly-cyclohexylamide 、 2-羟基-1-萘甲醛 以 甲醇 为溶剂， 生成 N-<(2-Hydroxy-1-naphthyl)methylene>-(S)-phenylglycine cyclohexylamide
  参考文献：
  名称：

  A peptide-aluminum complex as a novel chiral Lewis acid. Asymmetric addition of cyanotrimethylsilane to aldehydes

  摘要：

  The enantioselective addition of cyanotrimethylsilane (TMSCN) to aldehydes promoted by the addition of a stoichiometric or catalytic amount of organoaluminum complexes of dipeptide esters or alpha-amino acid amides whose amino terminals are modified by a variety of protective groups is described. The reaction of benzaldehyde with TMSCN in the presence of a stoichiometric or catalytic amount of the complex prepared from N-[2-hydroxy-1-naphthyl)methylene]-(S)-valyl-(S)-phenylalanine methyl ester (1a) or N-1(2-hydroxy-1-naphthyl)-methylene]-(S)-valine cyclohexylamide (2a) and trimethylaluminum gives (R)-mandelonitrile in good yield with enantioselectivity as high as 71%. The reaction of cyclohexanecarbaldehyde in the presence of the aluminum complex of N-(1-methyl-2-acetyl-vinyl)-(S)-valine cyclohexylamide (3b) furnishes the corresponding (R)-cyanohydrin in 38% ee, and the reaction of 2,2-dimethylpropionaldehyde with the aluminum complex of N-(4-toluene-sulfonyl)-(S)-valyl-(S)-phenylalanine methyl ester (4a) gives the corresponding (S)-cyanohydrin in 67% ee.

  DOI：

  10.1021/jo00051a020