N-dansyl-1-azido-6-aminohexane | 1241473-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-dansyl-1-azido-6-aminohexane
• 英文别名: N-(6-Azidohexyl)-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 1241473-36-8
• 化学式: C₁₈H₂₅N₅O₂S
• 分子量: 375.495
• InChiKey: LWQGCQLELMREMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-dansyl-1-azido-6-aminohexane 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以78%的产率得到N-(6-氨基己基)-5-二甲基氨基萘-1-磺酰胺
  参考文献：
  名称：

  1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines

  摘要：

  Cyclization by double reductive amination of D-xylo-hexos-5-ulose with methyl 6-aminohexanoate gave (methoxycarbonyl)pentyl-1-deoxynojirimycin. Reaction of the terminal carboxylic acid with N-dansyl-1,6-diaminohexane provided the corresponding chain-extended fluorescent derivative. By reaction with bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Both compounds are strong inhibitors of D-glucosidases and could also be shown to distinctly improve, at sub-inhibitory concentrations, the activity of beta-glucocerebrosidase in a Gaucher fibroblast (N370S) cell-line through chaperoning of the enzyme to the lysosome. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.04.015
• 作为产物：
  描述：

  N-dansyl-O-mesyl-6-aminohexanol 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到N-dansyl-1-azido-6-aminohexane
  参考文献：
  名称：

  1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines

  摘要：

  Cyclization by double reductive amination of D-xylo-hexos-5-ulose with methyl 6-aminohexanoate gave (methoxycarbonyl)pentyl-1-deoxynojirimycin. Reaction of the terminal carboxylic acid with N-dansyl-1,6-diaminohexane provided the corresponding chain-extended fluorescent derivative. By reaction with bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Both compounds are strong inhibitors of D-glucosidases and could also be shown to distinctly improve, at sub-inhibitory concentrations, the activity of beta-glucocerebrosidase in a Gaucher fibroblast (N370S) cell-line through chaperoning of the enzyme to the lysosome. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.04.015