methyl 2-acetamido-2-(3-methyl-1H-indol-2-yl)propanoate | 1337962-77-2

• 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: methyl 2-acetamido-2-(3-methyl-1H-indol-2-yl)propanoate
• CAS: 1337962-77-2
• 化学式: C₁₅H₁₈N₂O₃
• 分子量: 274.32
• InChiKey: WMCXWNJDLPXXGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基吲哚 、 2-乙酰胺基丙烯酸甲酯 在 O,O'(2,2'-biphenylylene)phosphoric acid 、 sodium sulfate 作用下， 以 甲苯 为溶剂， 反应 60.0h， 以31%的产率得到methyl 2-acetamido-2-(3-methyl-1H-indol-2-yl)propanoate
  参考文献：
  名称：

  Organocatalytic synthesis of α-quaternary amino acid derivatives via aza-Friedel–Crafts alkylation of indoles with simple α-amidoacrylates

  摘要：

  The first (organo)catalytic method for regio- and chemoselective aza-Friedel-Crafts (FC) alkylation of indoles and pyrroles with commercially available methyl alpha-acetamidoacrylates has been discovered. It minimizes/eliminates common competing reactions that occur due to the high and multiatom-nucleophilic character of indole and pyrrole. Diverse quaternary alpha-amino acids were successfully prepared in good yield and high selectivity using low catalyst loading. The enantioselective variant using BINOL-derived phosphoric acids was also explored with indole providing the desired F-C alkylation product with moderate enantioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.039

文献信息

• Organocatalytic synthesis of α-quaternary amino acid derivatives via aza-Friedel–Crafts alkylation of indoles with simple α-amidoacrylates
  作者：Marika Righi、Francesca Bartoccini、Simone Lucarini、Giovanni Piersanti

  DOI：10.1016/j.tet.2011.08.039

  日期：2011.10

  The first (organo)catalytic method for regio- and chemoselective aza-Friedel-Crafts (FC) alkylation of indoles and pyrroles with commercially available methyl alpha-acetamidoacrylates has been discovered. It minimizes/eliminates common competing reactions that occur due to the high and multiatom-nucleophilic character of indole and pyrrole. Diverse quaternary alpha-amino acids were successfully prepared in good yield and high selectivity using low catalyst loading. The enantioselective variant using BINOL-derived phosphoric acids was also explored with indole providing the desired F-C alkylation product with moderate enantioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.