(2R)-2-amino-2-(1H-indol-3-yl)-N-methylacetamide

• 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: (2R)-2-amino-2-(1H-indol-3-yl)-N-methylacetamide
• 化学式: C₁₁H₁₃N₃O
• 分子量: 203.244
• InChiKey: CDDRDZJWOHWUHD-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Fmoc-甘氨酸 、 (2R)-2-amino-2-(1H-indol-3-yl)-N-methylacetamide 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 (9H-fluoren-9-yl)methyl (R)-(2-((1-(1H-indol-3-yl)-2-(methylamino)-2-oxoethyl)amino)-2-oxoethyl)carbamate
  参考文献：
  名称：

  Direct Enantioselective Indolylation of Peptidyl Imine for the Synthesis of Indolyl Glycine-Containing Peptides

  摘要：

  A novel synthetic method involving the direct application of a catalytic asymmetric reaction to peptides was developed. The conditions optimized for the model asymmetric reaction of a simple alpha-imino amide with an indole derivative were successfully applied to an asymmetric Friedel Crafts reaction of alpha-imino peptide possessing a hydrophobic anchor to afford the indolyl glycine-containing peptide. This novel strategy will be of great value for the synthesis of the biologically important peptides bearing varieties of unnatural amino acids.

  DOI：

  10.3987/com-18-s(t)86
• 作为产物：
  描述：

  (R)-2-(1H-indol-3-yl)-N-methyl-2-(((2-nitrophenyl)thio)amino)acetamide 在 2-巯基吡啶 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 (2R)-2-amino-2-(1H-indol-3-yl)-N-methylacetamide
  参考文献：
  名称：

  Direct Enantioselective Indolylation of Peptidyl Imine for the Synthesis of Indolyl Glycine-Containing Peptides

  摘要：

  A novel synthetic method involving the direct application of a catalytic asymmetric reaction to peptides was developed. The conditions optimized for the model asymmetric reaction of a simple alpha-imino amide with an indole derivative were successfully applied to an asymmetric Friedel Crafts reaction of alpha-imino peptide possessing a hydrophobic anchor to afford the indolyl glycine-containing peptide. This novel strategy will be of great value for the synthesis of the biologically important peptides bearing varieties of unnatural amino acids.

  DOI：

  10.3987/com-18-s(t)86