2-((4-Methylquinolin-2-yl)amino)acetic acid | 1427027-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-((4-Methylquinolin-2-yl)amino)acetic acid
• 英文别名: 2-[(4-methylquinolin-2-yl)amino]acetic acid
• CAS: 1427027-44-8
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: PXLBMADFJUGGFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基-2-氯-喹啉 、 甘氨酸乙酯盐酸盐 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以70%的产率得到ethyl 2-((4-methylquinolin-2-yl)amino)acetate
  参考文献：
  名称：

  N-Heteroarylation of Chiral α-Aminoesters by Means of Palladium-Catalyzed Buchwald–Hartwig Reaction

  摘要：

  N-Heteroaryl-alpha-amino acid derivatives are valuable pharmacological agents as peptidomimetics. Classical SNAr methods using acid catalysis and elevated temperatures could not be extended to various alpha-amino acids and fairly electrophilic heterocyclic partners. Here, we report a mild and versatile method of N-heteroarylation of chiral alpha-aminoesters without racemization, involving Buchwald-Hartwig conditions. It could be extended to various a-amino acids and azines. This efficient N-heteroarylation leads to (i) a chemical library of putative peptidomimetics combining diverse azaheterocycles with the chiral alpha-aminoesters and their corresponding derivatives (amides, alcohols, etc.) and (ii) arginine derivatives designed as NPFF receptor ligancls.

  DOI：

  10.1021/jo4011427

文献信息

• <i>N</i>-Heteroarylation of Chiral α-Aminoesters by Means of Palladium-Catalyzed Buchwald–Hartwig Reaction
  作者：Hassan Hammoud、Martine Schmitt、Emilie Blaise、Frédéric Bihel、Jean-Jacques Bourguignon

  DOI：10.1021/jo4011427

  日期：2013.8.16

  N-Heteroaryl-alpha-amino acid derivatives are valuable pharmacological agents as peptidomimetics. Classical SNAr methods using acid catalysis and elevated temperatures could not be extended to various alpha-amino acids and fairly electrophilic heterocyclic partners. Here, we report a mild and versatile method of N-heteroarylation of chiral alpha-aminoesters without racemization, involving Buchwald-Hartwig conditions. It could be extended to various a-amino acids and azines. This efficient N-heteroarylation leads to (i) a chemical library of putative peptidomimetics combining diverse azaheterocycles with the chiral alpha-aminoesters and their corresponding derivatives (amides, alcohols, etc.) and (ii) arginine derivatives designed as NPFF receptor ligancls.