1-[2-(1,3-苯并恶唑-2-基)苯基]-3-苯基脲 | 918329-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-[2-(1,3-苯并恶唑-2-基)苯基]-3-苯基脲
• 英文名称: 1-(2-(benzo[d]oxazol-2-yl)phenyl)-3-phenylurea
• 英文别名: N-[2-(1,3-Benzoxazol-2-yl)phenyl]-N'-phenylurea；1-[2-(1,3-benzoxazol-2-yl)phenyl]-3-phenylurea
• CAS: 918329-12-1
• 化学式: C₂₀H₁₅N₃O₂
• 分子量: 329.358
• InChiKey: YQAYCMNADYMMEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异氰酸苯酯 、 2-(1,3-苯并恶唑-2-基)苯胺 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以92%的产率得到1-[2-(1,3-苯并恶唑-2-基)苯基]-3-苯基脲
  参考文献：
  名称：

  Fluorescence Sensing of Anions Based on Inhibition of Excited-State Intramolecular Proton Transfer

  摘要：

  [GRAPHICS]Condensation of 2-(2'-aminophenyl)benzoxazole with p-toluenesulfonyl chloride and phenyl isocyanate yields two new anion sensors (TABO and PUBO), which can undergo excited-state intramolecular proton transfer (ESIPT) upon excitation. For the acid receptor TABO, the ESIPT process can be readily disturbed by basic anions such as F-, CH3COO-, and H2PO4- by deprotonating the sulfonamide unit, whereas in the case of PUBO, a good hydrogen-bonding donor, the ESIPT process is inhibited either by the fluoride-induced deprotonation of the urea unit or by the formation of a strong CH3COO--urea intermolecular hydrogen bond complex, and these two types of inhibition mechanisms consequently result in different ratiometric responses. But other anions with less hydrogen-bonding acceptor abilities cannot inhibit the ESIPT. Interestingly, the different inhibition abilities of F-, CH3COO-, and H2PO4- produce different spectral behaviors in PUBO, so this new sensor successfully distinguishes the subtle difference in these three anionic substrates of similar basicity and surface charge density.

  DOI：

  10.1021/jo061634c