(4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxo-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]-nonadeca-1(19),15,17-trien-11-one | 1350538-43-0

• 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: (4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxo-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,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxy-3,10,13,19-tetraazatricyclo[13,3,1,0]-nonadeca-1(19),15,17-trien-11-one
• CAS: 1350538-43-0
• 化学式: C₃₄H₃₄N₆O₁₀S₂
• 分子量: 750.81
• InChiKey: QADXJIHDSHCXFQ-WUNLWTINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  52.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  217.08
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxo-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]-nonadeca-1(19),15,17-trien-11-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2-巯基乙醇 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以91%的产率得到(4R,9R)-12-benzyl-19-oxo-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
• 作为产物：
  描述：

  (S)-2-(2-nitrophenylsulfonamido)-3-phenylpropanoic acid 在 4-二甲氨基吡啶 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 20.0h， 生成 (4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxo-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