(S)-4-苯基-3-对甲苯噁唑啉-2-酮 | 572923-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-4-苯基-3-对甲苯噁唑啉-2-酮
• 中文别名: 3-氨基-3-(2-苯甲酰苯)-丙酸
• 英文名称: 4-phenyl-3-(p-tolyl)-oxazolidin-2-one
• 英文别名: (S)-4-Phenyl-3-p-tolyloxazolidin-2-one；(4S)-3-(4-methylphenyl)-4-phenyl-1,3-oxazolidin-2-one
• CAS: 572923-05-8
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: QENWQHDTOBJPJL-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-苯基-3-对甲苯噁唑啉-2-酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以84%的产率得到(S)-2-苯基-2-对甲苯氨基乙醇
  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
• 作为产物：
  描述：

  对氯甲苯 、 (S)-4-苯基-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50%的产率得到(S)-4-苯基-3-对甲苯噁唑啉-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

• Cu-Catalyzed N-Arylation of Oxazolidinones:  An Efficient Synthesis of the κ-Opioid Receptor Agonist CJ-15161
  作者：Arun Ghosh、Janice E. Sieser、Stéphane Caron、Michel Couturier、Kristina Dupont-Gaudet、Melina Girardin

  DOI：10.1021/jo052060z

  日期：2006.2.1

  An efficient method for intermolecular N-arylation of oxazolidinones using catalytic copper in the presence of a bidentate ligand is reported. The conditions allow the use of copper and can be used to prepare enantiopure N-aryl beta-amino alcohols. A short, scalable synthesis of CJ-15,161 is also reported. The required amines were obtained from the precursor alpha-amino acids or, more conveniently, from the corresponding 1,2-amino alcohols.