(S)-2-(6-chloropyridin-3-yl)-4-phenyl-1,3-oxazoline | 1424273-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-2-(6-chloropyridin-3-yl)-4-phenyl-1,3-oxazoline
• 英文别名: (4S)-2-(6-chloropyridin-3-yl)-4-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 1424273-32-4
• 化学式: C₁₄H₁₁ClN₂O
• 分子量: 258.707
• InChiKey: NWTAYNATNSWUQL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氯烟酸 、 L-苯甘氨醇 在 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 13.0h， 以19%的产率得到(S)-2-(6-chloropyridin-3-yl)-5-phenyl-1,3-oxazoline
  参考文献：
  名称：

  Study on the tandem synthesis of optically active 2-substituted 4 (or 5)-phenyl-1,3-oxazolines

  摘要：

  Optically active (S)-2-aryl-4 (or 5)-phenyl-1,3-oxazolines and (S)-2-fluoroalkyl-4-phenyl-1,3-oxazolines were synthesized from a tandem one-pot reaction of (S)-2-amino-2-phenylethanol with a corresponding carboxylic acid in toluene at 90 degrees C in the presence of PPh3/CBr4 and excess Et3N. The use of aromatic carboxylic acids were determined to proceed through N-(2-bromo-1-phenyl-ethyl)-arylamides 5 and N-aroyl aziridine intermediates 6, which resulted in the formation of (S)-2-aryl-4-phenyl-1,3-oxazolines and (S)-2-aryl-5-phenyl-1,3-oxazolines, respectively. Concurrently, the reaction with fluorinated aliphatic carboxylic acid substrates proceeded via N-(2-hydroxy-1-phenyl-ethyl)-fluoroalkyl amide intermediates 8, which were converted into N-(2-bromo-1-phenyl-ethyl)-fluoroalkyl amide intermediates 9, and then into (S)-2-fluoroalkyl-4-phenyl-1,3-oxazolines as final products. Reaction mechanisms that mainly passed through the formation of aziridine intermediates 6 in the reaction with aromatic carboxylic acids and the formation of fluoroalkyl amide intermediates 8 and 9 in the reaction with fluorinated aliphatic carboxylic acid were proposed. The acidities of the carboxylic acids that were employed were found to play a key role in the selective formation of various intermediates during this reaction. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.078