N-(p-Toluenesulfonyl)-(S)-valine cyclohexylamide | 145192-67-2

• 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-(p-Toluenesulfonyl)-(S)-valine cyclohexylamide
• 英文别名: (2S)-N-cyclohexyl-3-methyl-2-[(4-methylphenyl)sulfonylamino]butanamide
• CAS: 145192-67-2
• 化学式: C₁₈H₂₈N₂O₃S
• 分子量: 352.498
• InChiKey: KPRMZSZVPWZQNW-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(p-toluenesulfonyl)-L-valine 、 环己胺 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(p-Toluenesulfonyl)-(S)-valine 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

文献信息

• A peptide-aluminum complex as a novel chiral Lewis acid. Asymmetric addition of cyanotrimethylsilane to aldehydes
  作者：Hiroshi Ohno、Hideaki Nitta、Kenzo Tanaka、Atsunori Mori、Shohei Inoue

  DOI：10.1021/jo00051a020

  日期：1992.12

  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.