N-(2-aminocyclohexyl)-2-nitrobenzene-1-sulfonamide | 1350538-33-8

• 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: N-(2-aminocyclohexyl)-2-nitrobenzene-1-sulfonamide
• 英文别名: N-[(1R,2R)-2-aminocyclohexyl]-2-nitrobenzene-1-sulfonamide；N-[(1R,2R)-2-aminocyclohexyl]-2-nitrobenzenesulfonamide
• CAS: 1350538-33-8
• 化学式: C₁₂H₁₇N₃O₄S
• 分子量: 299.351
• InChiKey: DFQDKUQFMHCQSB-NXEZZACHSA-N

物化性质

• 沸点：
  482.3±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 、 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
• 作为产物：
  描述：

  trans-1,2-(R,R)-diammoniumcyclohexane tartrate 在 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.67h， 生成 N-(2-aminocyclohexyl)-2-nitrobenzene-1-sulfonamide
  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.