N-(4-nitrobenzenesulfonyl)-1,3-diphenylpropan-2-amine | 348593-03-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(4-nitrobenzenesulfonyl)-1,3-diphenylpropan-2-amine
• 英文别名: N-(1,3-diphenylpropan-2-yl)-4-nitrobenzenesulfonamide
• CAS: 348593-03-3
• 化学式: C₂₁H₂₀N₂O₄S
• 分子量: 396.467
• InChiKey: XCSDHVYLYWJSND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-nitrobenzenesulfonyl)-2-benzylaziridine 、 苯硼酸 在 3-氯苯酚 、 三(1-萘基)膦 、 caesium carbonate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以69%的产率得到N-(4-nitrobenzenesulfonyl)-1,3-diphenylpropan-2-amine
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of N-Sulfonylaziridines with Boronic Acids

  摘要：

  A mild palladium-catalyzed cross-coupling of unsubstituted and 2-alkyl-substituted aziridines with arylboronic acid nucleophiles is presented. The reaction is highly regioselective and compatible with diverse functionality. A catalytic amount of base, a sterically demanding triarylphosphine ligand, and a phenol additive are critical to the success of the reaction. Coupling of a deuterium-labeled substrate established that ring opening of the aziridine occurs with inversion of stereochemistry.

  DOI：

  10.1021/ja410686v

文献信息

• Palladium-Catalyzed Cross-Coupling of <i>N</i>-Sulfonylaziridines with Boronic Acids
  作者：Megan L. Duda、Forrest E. Michael

  DOI：10.1021/ja410686v

  日期：2013.12.11

  A mild palladium-catalyzed cross-coupling of unsubstituted and 2-alkyl-substituted aziridines with arylboronic acid nucleophiles is presented. The reaction is highly regioselective and compatible with diverse functionality. A catalytic amount of base, a sterically demanding triarylphosphine ligand, and a phenol additive are critical to the success of the reaction. Coupling of a deuterium-labeled substrate established that ring opening of the aziridine occurs with inversion of stereochemistry.