4-(2-oxo-4-phenyl-1,2,3-oxathiazolidin-3-yl)-N-(propyl)benzamide | 876747-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-oxo-4-phenyl-1,2,3-oxathiazolidin-3-yl)-N-(propyl)benzamide
• 英文别名: 4-[(4S)-2-oxo-4-phenyloxathiazolidin-3-yl]-N-propylbenzamide
• CAS: 876747-67-0
• 化学式: C₁₈H₂₀N₂O₃S
• 分子量: 344.434
• InChiKey: HAMCNVWQVDKLPT-BPNWFJGMSA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-oxo-4-phenyl-1,2,3-oxathiazolidin-3-yl)-N-(propyl)benzamide 在 ruthenium trichloride 、 sodium tetrahydroborate 、 sodium periodate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 benzoic acid 1-{2-[methyl(4-(propylcarbamoyl)phenyl)amino]-2-phenylethyl}pyrrolidin-3-yl ester
  参考文献：
  名称：

  Cu-Catalyzed N-Arylation of Oxazolidinones:  An Efficient Synthesis of the κ-Opioid Receptor Agonist CJ-15161

  摘要：

  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.

  DOI：

  10.1021/jo052060z
• 作为产物：
  描述：

  (S)-4-苯基-2-恶唑烷酮 在 吡啶 、 sodium hydroxide 、 copper(l) iodide 、 氯化亚砜 、 potassium carbonate 、 1,2-二氨基环己烷 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 4-(2-oxo-4-phenyl-1,2,3-oxathiazolidin-3-yl)-N-(propyl)benzamide
  参考文献：
  名称：

  Cu-Catalyzed N-Arylation of Oxazolidinones:  An Efficient Synthesis of the κ-Opioid Receptor Agonist CJ-15161

  摘要：

  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.

  DOI：

  10.1021/jo052060z

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.