2-(2,3,5,6-tetrafluoro-4-methoxyphenyl)benzoxazole | 521982-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,3,5,6-tetrafluoro-4-methoxyphenyl)benzoxazole
• 英文别名: 2-(2,3,5,6-Tetrafluoro-4-methoxyphenyl)-1,3-benzoxazole
• CAS: 521982-04-7
• 化学式: C₁₄H₇F₄NO₂
• 分子量: 297.209
• InChiKey: HNXOJETXLCHISZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2,3,5,6-tetrafluoro-4-methoxyphenyl)benzoxazole 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以91%的产率得到2-(3,5,6-trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole
  参考文献：
  名称：

  Application of 2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole and -benzothiazole to Fluorescent Probes Sensing pH and Metal Cations

  摘要：

  2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole (3) and benzothiazole analogue (4) are prepared by the two-step procedures from the corresponding 2-(pentafluorophenyl)benzazoles. Benzoxazole 3 is applicable to a fluorescent probe sensing magnesium cation, and 4 is suitable for sensing zinc cation. Both fluorophores 3 and 4 are sensitive to the pH change at pH 7-8, resulting in large fluorescence enhancement under basic conditions. Their high sensitivity to pH and selectivity in metal cations are ascribed to the high acidity of the fluorophenol moiety.

  DOI：

  10.1021/jo010462a
• 作为产物：
  描述：

  sodium methylate 、 2-(perfluorophenyl)benzo[d]oxazole 以 甲醇 为溶剂， 反应 2.0h， 以76%的产率得到2-(2,3,5,6-tetrafluoro-4-methoxyphenyl)benzoxazole
  参考文献：
  名称：

  Application of 2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole and -benzothiazole to Fluorescent Probes Sensing pH and Metal Cations

  摘要：

  2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole (3) and benzothiazole analogue (4) are prepared by the two-step procedures from the corresponding 2-(pentafluorophenyl)benzazoles. Benzoxazole 3 is applicable to a fluorescent probe sensing magnesium cation, and 4 is suitable for sensing zinc cation. Both fluorophores 3 and 4 are sensitive to the pH change at pH 7-8, resulting in large fluorescence enhancement under basic conditions. Their high sensitivity to pH and selectivity in metal cations are ascribed to the high acidity of the fluorophenol moiety.

  DOI：

  10.1021/jo010462a

文献信息

• Novel fluorescent 2-(2-aminofluorophenyl)benzoxazoles: Syntheses and photophysical properties
  作者：Kiyoshi Tanaka、Tomohiro Komiya

  DOI：10.1002/jhet.5570390629

  日期：2002.11

  2-(2-Amino-3,4,5,6-tetrafluorophenyl)benzoxazole (2) absorbs in long wavelength band (λabsmax = 346 nm in methanol) and in the normal wavelength band (λabsmax = 285.5 nm), and emits blue fluorescence. The emission intensity is highly affected by the solvent polarity and is large in a polar solvent such as methanol. 2-(2-Pentafluorobenzamido-3,4,5,6- tetrafluorophenyl)benzoxazole (5) emits green fluorescence

  2-（2-氨基-3,4,5,6-四氟苯基）苯并恶唑（2）在长波长带（在甲醇中λabs max = 346 nm）和正常波长带（λabs max = 285.5 nm）中吸收，并发出蓝色荧光。发射强度受溶剂极性的影响很大，在极性溶剂（如甲醇）中较大。2-（2-五氟苯甲酰胺基-3,4,5,6-四氟苯基）苯并恶唑（5）发出绿色荧光，同时发出约380 nm的短波长，其相对强度取决于溶剂极性。在非极性溶剂（如氯仿和甲苯）中，绿色荧光增强，从而导致相当大的斯托克斯位移。