(4R,9R)-3,13-bis(2-nitrobenzenesulfonyl)-19-oxy-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1(19),15,17-trien-11-one | 1350538-45-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (4R,9R)-3,13-bis(2-nitrobenzenesulfonyl)-19-oxy-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1(19),15,17-trien-11-one
• 英文别名: (4R,9R)-3,13-bis(2-nitrobenzenesulfonyl)-19-oxy-3,10,13,19-tetraazatricyclo[13,3,1,0]nonadeca-1(19),15,17-trien-11-one；(4R,9R)-3,13-bis[(2-nitrophenyl)sulfonyl]-19-oxido-3,10,13-triaza-19-azoniatricyclo[13.3.1.04,9]nonadeca-1(18),15(19),16-trien-11-one
• CAS: 1350538-45-2
• 化学式: C₂₇H₂₈N₆O₁₀S₂
• 分子量: 660.686
• InChiKey: VQEANPMKERYXQT-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  45
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  238
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2,6-二氯甲基吡啶 在 双氧水 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 8.0h， 生成 (4R,9R)-3,13-bis(2-nitrobenzenesulfonyl)-19-oxy-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1(19),15,17-trien-11-one
  参考文献：
  名称：

  Ready Available Chiral Azapyridinomacrocycles N-Oxides; First Results as Lewis Base Catalysts in Asymmetric Allylation of p-Nitrobenzaldehyde

  摘要：

  We report here the straightforward synthesis of the first series of enantiomerically pure azapyridinomacrocycles N-oxides containing a cyclohexyl chiral moiety. These compounds were readily obtained in good overall yields by a convergent synthesis using natural amino acids as starting building blocks and macrocyclisation as the key step. This method is rapid, efficient and suitable for the introduction of various substituents at the macrocyclic skeleton. Finally, the compounds were tested as organocatalysts for the enantioselective allylation of p-nitrobenzaldehyde with allyltrichlorosilane.

  DOI：

  10.3987/com-11-12249

文献信息

• Ready Available Chiral Azapyridinomacrocycles N-Oxides; First Results as Lewis Base Catalysts in Asymmetric Allylation of p-Nitrobenzaldehyde
  作者：Maité Sylla-Iyarreta Veitía、Clotilde Ferroud、Mounia Joudat、Mathieu Wagner、Annie Falguières、Alain Guy

  DOI：10.3987/com-11-12249

  日期：——

  We report here the straightforward synthesis of the first series of enantiomerically pure azapyridinomacrocycles N-oxides containing a cyclohexyl chiral moiety. These compounds were readily obtained in good overall yields by a convergent synthesis using natural amino acids as starting building blocks and macrocyclisation as the key step. This method is rapid, efficient and suitable for the introduction of various substituents at the macrocyclic skeleton. Finally, the compounds were tested as organocatalysts for the enantioselective allylation of p-nitrobenzaldehyde with allyltrichlorosilane.