(S)-3-(3-乙酰基苯基)-4-乙基噁唑啉-2-酮 | 572923-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)-3-(3-乙酰基苯基)-4-乙基噁唑啉-2-酮
• 中文别名: 4-苄基-3-氯-苯甲酸甲酯
• 英文名称: 3-(3-acetyl-phenyl)-4-ethyl-oxazolidin-2-one
• 英文别名: (S)-3-(3-Acetylphenyl)-4-ethyloxazolidin-2-one；(4S)-3-(3-acetylphenyl)-4-ethyl-1,3-oxazolidin-2-one
• CAS: 572923-14-9
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: OHCCHBFAKAMJAY-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氯苯乙酮 、 (4S)-4-乙基-2-恶唑烷酮 在 tris(dibenzylideneacetone)dipalladium (0) 、 caesium carbonate 、 2-(二叔丁基膦)联苯 作用下， 以 甲苯 为溶剂， 反应 17.0h， 以94%的产率得到(S)-3-(3-乙酰基苯基)-4-乙基噁唑啉-2-酮
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis of N-Aryloxazolidinones from Aryl Chlorides

  摘要：

  An efficient method for intermolecular N-arylation of oxazolidinones using Pd(2)dba(3) and various phosphine ligands in the presence of a weak base is reported. The conditions allow the use of cheaper aryl chlorides containing functionalities such as enolizable ketones, amides, etc., which would be incompatible with other coupling methods. The coupling reaction can be used to prepare enantiopure N-aryl beta-amino alcohols. Depending on the stereoelectronic nature of the aryl chloride, careful choice of ligand was necessary for the success of these reactions.

  DOI：

  10.1021/ol034428p

文献信息

• Palladium-Catalyzed Synthesis of <i>N-</i>Aryloxazolidinones from Aryl Chlorides
  作者：Arun Ghosh、Janice E. Sieser、Maxime Riou、Weiling Cai、Luis Rivera-Ruiz

  DOI：10.1021/ol034428p

  日期：2003.6.1

  An efficient method for intermolecular N-arylation of oxazolidinones using Pd(2)dba(3) and various phosphine ligands in the presence of a weak base is reported. The conditions allow the use of cheaper aryl chlorides containing functionalities such as enolizable ketones, amides, etc., which would be incompatible with other coupling methods. The coupling reaction can be used to prepare enantiopure N-aryl beta-amino alcohols. Depending on the stereoelectronic nature of the aryl chloride, careful choice of ligand was necessary for the success of these reactions.