5-Dansylamino-1-pentanol | 52683-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Dansylamino-1-pentanol
• 英文别名: 5-(dimethylamino)-N-(5-hydroxypentyl)naphthalene-1-sulfonamide
• CAS: 52683-73-5
• 化学式: C₁₇H₂₄N₂O₃S
• 分子量: 336.455
• InChiKey: YHLRQXBWHWXAPT-UHFFFAOYSA-N

物化性质

• 沸点：
  515.3±60.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  78
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Dansylamino-1-pentanol 在 二异丁基氢化铝 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 生成 5-(dimethylamino)-N-(5-sulfanylpentyl)naphthalene-1-sulfonamide
  参考文献：
  名称：

  Fluorophore-Labeled S-Nitrosothiols

  摘要：

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.

  DOI：

  10.1021/jo015658p
• 作为产物：
  描述：

  5-氨基-1-戊醇 、 丹酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-Dansylamino-1-pentanol
  参考文献：
  名称：

  Fluorophore-Labeled S-Nitrosothiols

  摘要：

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.

  DOI：

  10.1021/jo015658p

文献信息

• Carboaminoxylation as a Tool to Prepare Functionalized Polymeric Materials: Introduction of Biologically Important Residues by Metal-Free Radical CC Coupling Reactions
  作者：Jean-Pierre Lindner、Armido Studer

  DOI：10.1002/chem.201003163

  日期：2011.4.4

  Making a radical change! Radical CC bond formation by thermal carboaminoxylation of alkoxyamines was used for functionalization of unsaturated macromolecular systems with biologically important residues (R; see scheme). The synthesized dendritic mannose‐containing glycopolymers show very strong inhibition of the lectin Concanavalin A as measured by an enzyme‐linked lectin assay.

  做出根本性的改变！自由基Ç 由烷氧基胺的热carboaminoxylation C键的形成被用于不饱和大分子系统的官能化与生物学上重要的残基（R;参见方案）。合成的树突状含甘露糖糖聚合物对凝集素伴刀豆球蛋白A表现出非常强的抑制作用，这是通过酶联凝集素测定法测得的。
• Fluorophore-Labeled <i>S</i>-Nitrosothiols
  作者：Xinchao Chen、Zhong Wen、Ming Xian、Kun Wang、Niroshan Ramachandran、Xiaoping Tang、H. Bernhard Schlegel、Bulent Mutus、Peng George Wang

  DOI：10.1021/jo015658p

  日期：2001.9.1

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.