1-(2-oxo-2H-chromen-6-yl)-3-phenyl-urea | 6513-73-1

• 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: 1-(2-oxo-2H-chromen-6-yl)-3-phenyl-urea
• 英文别名: 6-(N'-phenyl-ureido)-coumarin；6-(N'-Phenyl-ureido)-cumarin；6-<3-Phenyl-ureido>-cumarin；1-(2-Oxochromen-6-yl)-3-phenylurea
• CAS: 6513-73-1
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: QLIFPIVWYKODSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2H-1-苯并吡喃-2-酮,6-氨基- 在 光气 、 甲苯 、 苯 作用下， 生成 1-(2-oxo-2H-chromen-6-yl)-3-phenyl-urea
  参考文献：
  名称：

  Dey; Seshadri, Journal of the Indian Chemical Society, 1931, vol. 8, p. 293,297

  摘要：

  DOI：

文献信息

• A Dual Emissive Coumarin–urea Derivative with an Electron‐withdrawing Substituent in the Presence of Acetate Anion
  作者：Tomoyuki Shinoda、Yoshinobu Nishimura、Tatsuo Arai

  DOI：10.1111/php.13165

  日期：2020.1

  AbstractWe investigated the fluorescent properties, including the excited‐state intermolecular proton transfer, of urea derivatives comprising a coumarin ring, which is a widely used fluorophore. We prepared two different coumarin–urea derivatives, 6CU and 7CU, which bear a urea‐based substituent at the 6 and 7 positions of a coumarin ring, respectively. In the presence of the acetate ion, 7CU showed additional tautomer fluorescence emission with respect to 6CU, indicating that tautomer formation depends on the positions of the urea‐based substituent on the coumarin ring. Thus, the resonance structures of urea derivatives might play an important role in the behavior of dual fluorescence, which is an important phenomenon applicable to photochemical anion sensing. Moreover, in order to further improve the fluorescence properties of the mentioned derivatives, a CF3 group was introduced in a phenyl ring opposite to a coumarin ring. The fluorescence quantum yield of 7CUCF3 thus synthesized was 65 times as large as that of 7CU, an observation that renders 7CUCF3 a suitable anion sensor candidate. The results of this study will contribute to the development of new molecular designs for highly fluorescent sensing.