2-amino-2-(furan-3-yl)ethanoic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-2-(furan-3-yl)ethanoic acid
• 英文别名: 2-azaniumyl-2-(furan-3-yl)acetate
• 化学式: C₆H₇NO₃
• mdl: MFCD01859902
• 分子量: 141.126
• InChiKey: PGRLXLPRSSHTCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  76.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-2-(furan-3-yl)ethanoic acid 在 氯化亚砜 、 三乙胺 、 二异丙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 19.5h， 生成
  参考文献：
  名称：

  Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-Isocyanoacetates, Phenyl Vinyl Selenones, and Water

  摘要：

  Reaction of alpha-substituted alpha-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.

  DOI：

  10.1021/ja506031h

文献信息

• Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-Isocyanoacetates, Phenyl Vinyl Selenones, and Water
  作者：Thomas Buyck、Qian Wang、Jieping Zhu

  DOI：10.1021/ja506031h

  日期：2014.8.13

  Reaction of alpha-substituted alpha-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.