(S)-ethyl 2-((4-methylquinolin-2-yl)amino)-3-phenylpropanoate | 1448586-27-3

• 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: (S)-ethyl 2-((4-methylquinolin-2-yl)amino)-3-phenylpropanoate
• 英文别名: ethyl (2S)-2-[(4-methylquinolin-2-yl)amino]-3-phenylpropanoate
• CAS: 1448586-27-3
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: DOVZCSSARIDWKM-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 2-((4-methylquinolin-2-yl)amino)-3-phenylpropanoate 、 (S)-(-)-α-甲氧基-α-(三氟甲基)苯乙酸 以 氘代氯仿 为溶剂， 生成
  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
• 作为产物：
  描述：

  4-甲基-2-氯-喹啉 、 L-苯丙氨酸乙酯盐酸盐 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以86%的产率得到(S)-ethyl 2-((4-methylquinolin-2-yl)amino)-3-phenylpropanoate
  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.