7-Amino-N-(2-ethylamino)-4-methylcoumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-Amino-N-(2-ethylamino)-4-methylcoumarin
• 英文别名: 7-(2-Aminoethylamino)-4-methylchromen-2-one
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: FXBUQOVHLBHRHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-硝基苯酯碘乙酸 、 7-Amino-N-(2-ethylamino)-4-methylcoumarin 以 乙醚 为溶剂， 生成 7-Amino-N-(2-ethylaminocarbonyliodomethyl)-4-methylcoumarin
  参考文献：
  名称：

  Nucleobase-Specific Quenching of Fluorescent Dyes. 1. Nucleobase One-Electron Redox Potentials and Their Correlation with Static and Dynamic Quenching Efficiencies

  摘要：

  Intermolecular static and dynamic fluorescence quenching constants of eight coumarin derivatives by nucleobase derivatives have been determined in aqueous media. One common sequence of the quenching efficiency has been found for the nucleobases. The feasibility of a photoinduced electron transfer reaction for the nucleobase-specific quenching of fluorescent dyes is investigated by the calculation of the standard free energy changes with the Rehm-Weller equation. A complete set of one-electron redox potential data for the nucleobases are determined electrochemically in aprotic solvents for the first time, which are compared with values obtained by various other methods. Depending on the redox properties of the fluorescent dyes, the sequences of the quenching efficiencies can be rationalized by the orders of electrochemical oxidation potentials (vs NHE) of nucleosides (dG (+1.47 V) < dA ( dC approximate to dT < U (greater than or equal to +2.39 V)) and reduction potentials (de (( -2.76 V) < dA < dC approximate to dT < U (-2.07 V)). The correlation between the intermolecular dynamic quenching constants and the standard free energy of photoinduced electron transfer according to the classical Marcus equation indicates that photoinduced electron transfer is the rate-limiting step. However, an additional, water-specific gain of free energy between -0.5 and -0.9 eV shows that additional effects, like a coupled proton transfer and a hydrophobic effect, have to be considered, too. Furthermore, the capability of the nucleobases to form ground state complexes with fluorescent dyes is influenced by their redox potentials. The relevance of these observations to current efforts for DNA sequencing with a detection by laser-induced fluorescence and their application to other dyes are discussed.

  DOI：

  10.1021/jp951507c
• 作为产物：
  描述：

  7-氨基-4-甲基香豆素 、 2-溴乙胺氢溴酸盐 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以92%的产率得到7-Amino-N-(2-ethylamino)-4-methylcoumarin
  参考文献：
  名称：

  A coumarin–thiourea conjugate as a fluorescent probe for Hg(ii) in aqueous media with a broad pH range 2–12

  摘要：

  香豆素-硫脲缀合物 (1) 可作为水介质中 Hg2+ 的高选择性荧光探针。在较宽的 pH 范围（2-12）的水介质中添加 Hg2+ 后，探针 1 显示出选择性和定量的荧光减弱。从头算分子轨道计算表明，Hg2+ 诱导的硫脲部分脱硫促进了 Hg2+ 添加后荧光强度降低 1，从而导致激发态香豆素部分的分子内电荷转移 (ICT) 特性降低。

  DOI：

  10.1039/b924015b

文献信息

• A coumarin–thiourea conjugate as a fluorescent probe for Hg(ii) in aqueous media with a broad pH range 2–12
  作者：Yasuhiro Shiraishi、Shigehiro Sumiya、Takayuki Hirai

  DOI：10.1039/b924015b

  日期：——

  A coumarin–thiourea conjugate (1) behaves as a highly selective fluorescent probe for Hg2+ in aqueous media. The probe 1 shows selective and quantitative fluorescence decrease upon Hg2+ addition in aqueous media with a broad pH range, 2–12. Ab initio molecular orbital calculations reveal that the fluorescence decrease of 1 upon Hg2+ addition is promoted by a Hg2+-induced desulfurization of the thiourea moiety, leading to a decrease in an intramolecular charge transfer (ICT) character of the excited-state coumarin moiety.

  香豆素-硫脲缀合物 (1) 可作为水介质中 Hg2+ 的高选择性荧光探针。在较宽的 pH 范围（2-12）的水介质中添加 Hg2+ 后，探针 1 显示出选择性和定量的荧光减弱。从头算分子轨道计算表明，Hg2+ 诱导的硫脲部分脱硫促进了 Hg2+ 添加后荧光强度降低 1，从而导致激发态香豆素部分的分子内电荷转移 (ICT) 特性降低。
• Nucleobase-Specific Quenching of Fluorescent Dyes. 1. Nucleobase One-Electron Redox Potentials and Their Correlation with Static and Dynamic Quenching Efficiencies
  作者：Claus A. M. Seidel、Andreas Schulz、Markus H. M. Sauer

  DOI：10.1021/jp951507c

  日期：1996.1.1

  Intermolecular static and dynamic fluorescence quenching constants of eight coumarin derivatives by nucleobase derivatives have been determined in aqueous media. One common sequence of the quenching efficiency has been found for the nucleobases. The feasibility of a photoinduced electron transfer reaction for the nucleobase-specific quenching of fluorescent dyes is investigated by the calculation of the standard free energy changes with the Rehm-Weller equation. A complete set of one-electron redox potential data for the nucleobases are determined electrochemically in aprotic solvents for the first time, which are compared with values obtained by various other methods. Depending on the redox properties of the fluorescent dyes, the sequences of the quenching efficiencies can be rationalized by the orders of electrochemical oxidation potentials (vs NHE) of nucleosides (dG (+1.47 V) < dA ( dC approximate to dT < U (greater than or equal to +2.39 V)) and reduction potentials (de (( -2.76 V) < dA < dC approximate to dT < U (-2.07 V)). The correlation between the intermolecular dynamic quenching constants and the standard free energy of photoinduced electron transfer according to the classical Marcus equation indicates that photoinduced electron transfer is the rate-limiting step. However, an additional, water-specific gain of free energy between -0.5 and -0.9 eV shows that additional effects, like a coupled proton transfer and a hydrophobic effect, have to be considered, too. Furthermore, the capability of the nucleobases to form ground state complexes with fluorescent dyes is influenced by their redox potentials. The relevance of these observations to current efforts for DNA sequencing with a detection by laser-induced fluorescence and their application to other dyes are discussed.