ethyl 2-((4-methylquinolin-2-yl)amino)acetate | 1448586-23-9

• 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: ethyl 2-((4-methylquinolin-2-yl)amino)acetate
• 英文别名: Ethyl 2-[(4-methylquinolin-2-yl)amino]acetate；ethyl 2-[(4-methylquinolin-2-yl)amino]acetate
• CAS: 1448586-23-9
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: NRKILLHJVOCARR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基-2-氯-喹啉 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 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.