3-{4-[5-(4-Dimethylamino-phenyl)-oxazol-2-yl]-benzenesulfonylamino}-propionic acid | 203250-34-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-{4-[5-(4-Dimethylamino-phenyl)-oxazol-2-yl]-benzenesulfonylamino}-propionic acid
• 英文别名: 3-[[4-[5-[4-(Dimethylamino)phenyl]-1,3-oxazol-2-yl]phenyl]sulfonylamino]propanoic acid
• CAS: 203250-34-4
• 化学式: C₂₀H₂₁N₃O₅S
• 分子量: 415.47
• InChiKey: UNIZXFRPTPIYGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 3-{4-[5-(4-Dimethylamino-phenyl)-oxazol-2-yl]-benzenesulfonylamino}-propionic acid 在 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以92%的产率得到dapoxil 3-sulfonamidopropionic acid succinimidyl ester
  参考文献：
  名称：

  Fluorescent Molecular Probes II. The Synthesis, Spectral Properties and Use of Fluorescent Solvatochromic Dapoxyl Dyes

  摘要：

  Abstract— 2,5‐Diphenyloxazoles that embody a dimethylamino group at position 4 of the 5‐phenyl ring and a sulfonyl group at position 4 of the 2‐phenyl ring were prepared as new fluorescent solvatochromic dyes. In these molecules, there is a “push‐pull” electron transfer system from the 5‐phenyl moiety to the 2‐phenyl ring. These compounds show strong solvent‐dependent fluorescence that is well correlated with the empirical solvent polarity parameter ET (30). The solvent polarity dependence suggests that the fluorescence arises from an intramolecular charge transfer. The fluorescence‐environment dependence, long emission wavelength, large extinction coefficients, high fluorescence quantum yields and large Stokes shift of the fluorophores can be used to develop ultrasensitive fluorescent molecular probes to study a variety of biological events and processes.

  DOI：

  10.1111/j.1751-1097.1997.tb03168.x
• 作为产物：
  描述：

  dapoxylsulfonyl chloride 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3-{4-[5-(4-Dimethylamino-phenyl)-oxazol-2-yl]-benzenesulfonylamino}-propionic acid
  参考文献：
  名称：

  Fluorescent Molecular Probes II. The Synthesis, Spectral Properties and Use of Fluorescent Solvatochromic Dapoxyl Dyes

  摘要：

  Abstract— 2,5‐Diphenyloxazoles that embody a dimethylamino group at position 4 of the 5‐phenyl ring and a sulfonyl group at position 4 of the 2‐phenyl ring were prepared as new fluorescent solvatochromic dyes. In these molecules, there is a “push‐pull” electron transfer system from the 5‐phenyl moiety to the 2‐phenyl ring. These compounds show strong solvent‐dependent fluorescence that is well correlated with the empirical solvent polarity parameter ET (30). The solvent polarity dependence suggests that the fluorescence arises from an intramolecular charge transfer. The fluorescence‐environment dependence, long emission wavelength, large extinction coefficients, high fluorescence quantum yields and large Stokes shift of the fluorophores can be used to develop ultrasensitive fluorescent molecular probes to study a variety of biological events and processes.

  DOI：

  10.1111/j.1751-1097.1997.tb03168.x

文献信息

• Fluorescent Molecular Probes II. The Synthesis, Spectral Properties and Use of Fluorescent Solvatochromic Dapoxyl Dyes
  作者：Zhenjun Diwu、Yixin Lu、Cailan Zhang、Dieter H. Klaubert、Richard P. Haugland

  DOI：10.1111/j.1751-1097.1997.tb03168.x

  日期：1997.10

  Abstract— 2,5‐Diphenyloxazoles that embody a dimethylamino group at position 4 of the 5‐phenyl ring and a sulfonyl group at position 4 of the 2‐phenyl ring were prepared as new fluorescent solvatochromic dyes. In these molecules, there is a “push‐pull” electron transfer system from the 5‐phenyl moiety to the 2‐phenyl ring. These compounds show strong solvent‐dependent fluorescence that is well correlated with the empirical solvent polarity parameter ET (30). The solvent polarity dependence suggests that the fluorescence arises from an intramolecular charge transfer. The fluorescence‐environment dependence, long emission wavelength, large extinction coefficients, high fluorescence quantum yields and large Stokes shift of the fluorophores can be used to develop ultrasensitive fluorescent molecular probes to study a variety of biological events and processes.