6,6'-(3-azapenta-1,5-di-yl)-1',2,3,3',4,4'-hexa-O-benzylsucrose | 1415048-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-(3-azapenta-1,5-di-yl)-1',2,3,3',4,4'-hexa-O-benzylsucrose
• CAS: 1415048-93-9
• 化学式: C₅₈H₆₅NO₁₁
• 分子量: 952.154
• InChiKey: MRPFEKSULRKFAN-TWVITFGLSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  70.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  113.56
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  6,6'-(3-azapenta-1,5-di-yl)-1',2,3,3',4,4'-hexa-O-benzylsucrose 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以72%的产率得到6,6'-[3-aza(2-methoxy-2-oxoethyl)penta-1,5-di-yl]-1',2,3,3',4,4'-hexa-O-benzylsucrose
  参考文献：
  名称：

  Novel sucrose-based macrocyclic receptors for enantioselective recognition of chiral ammonium cations

  摘要：

  A new synthetic route to macrocyclic sucrose-based receptors with different substituents at the ring nitrogen atom is described. Very good enantioselectivity toward phenylethylammonium chloride was observed [a much stronger complex with the cation of the (S)-amine was formed] although the K-a values were low. Much higher K-a (1.4 x 10(4) M-1 in CDCI3/CD3OD) values of the complexes with aminoacid derivatives (especially valine) were found although this time the enantioselectivities were moderate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.003
• 作为产物：
  描述：

  6-O-(cyanomethyl)-1',2,3,3',4,4'-hexa-O-benzylsucrose 在 lithium aluminium tetrahydride 、 四丁基溴化铵 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 19.17h， 生成 6,6'-(3-azapenta-1,5-di-yl)-1',2,3,3',4,4'-hexa-O-benzylsucrose
  参考文献：
  名称：

  Novel sucrose-based macrocyclic receptors for enantioselective recognition of chiral ammonium cations

  摘要：

  A new synthetic route to macrocyclic sucrose-based receptors with different substituents at the ring nitrogen atom is described. Very good enantioselectivity toward phenylethylammonium chloride was observed [a much stronger complex with the cation of the (S)-amine was formed] although the K-a values were low. Much higher K-a (1.4 x 10(4) M-1 in CDCI3/CD3OD) values of the complexes with aminoacid derivatives (especially valine) were found although this time the enantioselectivities were moderate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.003