(4R,9R)-3,13-bis(2-nitrobenzenesulfonyl)-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1(19),15,17-trien-11-one | 1350538-39-4

• 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)-3,13-bis(2-nitrobenzenesulfonyl)-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)-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]-3,10,13,19-tetrazatricyclo[13.3.1.04,9]nonadeca-1(18),15(19),16-trien-11-one
• CAS: 1350538-39-4
• 化学式: C₂₇H₂₈N₆O₉S₂
• 分子量: 644.686
• InChiKey: KMFOGEPJOMIERI-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  44
• 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：
  225
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (4R,9R)-3,13-bis(2-nitrobenzenesulfonyl)-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1(19),15,17-trien-11-one 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以90%的产率得到(4R,9R)-3,10,13,19-tetrazatricyclo[13.3.1.04,9]nonadeca-1(18),15(19),16-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：

  N-(2-aminocyclohexyl)-2-nitrobenzene-1-sulfonamide 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 (4R,9R)-3,13-bis(2-nitrobenzenesulfonyl)-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

• Synthesis of an hexadentate tricyclic tetraazadiacetic ligand as precursor for MRI contrast enhancement agents
  作者：Fabienne Dioury、Clotilde Ferroud、Alain Guy、Marc Port

  DOI：10.1016/j.tet.2009.06.117

  日期：2009.9

  A tricyclic tetraazadiacetic compound, which is a rigidified derivative of cyclo-PCTA12 ligand with an oxo-ethylene bridge replacing an ethylene one, was prepared. The synthetic route involved the macrocyclization between an activated amido-disulfonamide and the 2,6-bis(bromomethyl)pyridine. The acetate side chains were grafted on the macrocyclic backbone to lead to the highly rigid tricyclic ligand in 34% overall yield in four steps from the linear amido-disulfonamide precursor. The corresponding Gd(III) and Mn(II) complexes were then prepared in order to evaluate their potential as contrast agent for MRI. (C) 2009 Elsevier Ltd. All rights reserved.