5-<5-fluoro-2-(methylthio)phenyl>imidazolidine-2,4-dione | 120144-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-<5-fluoro-2-(methylthio)phenyl>imidazolidine-2,4-dione
• 英文别名: 5-[5-fluoro-2-(methylthio)phenyl]imidazolidine-2,4-dione
• CAS: 120144-45-8
• 化学式: C₁₀H₉FN₂O₂S
• 分子量: 240.258
• InChiKey: CBDWXJQIMCZWPX-UHFFFAOYSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-<5-fluoro-2-(methylthio)phenyl>imidazolidine-2,4-dione 在 potassium permanganate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 30.0h， 以61%的产率得到5-(5-Fluoro-2-methylsulfonylphenyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Rotationally restricted mimics of rigid molecules: nonspirocyclic hydantoin aldose reductase inhibitors

  摘要：

  Sorbinil (1), a spirocyclic hydantoin, is a potent inhibitor of the enzyme aldose reductase. Simulation of the rigid spirocyclic ring orientation found in sorbinil was achieved with nonspirocyclic 5-[5'-chloro-2'-(alkylsulfonyl)-phenyl]hydantoins and 5-[5'-chloro-2'-[(N-alkylamino)sulfonyl]phenyl]hydantoins. The 2'-substituent (SO2R) was sufficiently large to hinder rotation of the hydantoin ring, forcing an orientation similar to that of a spirocyclic hydantoin. Calculated conformational preference, X-ray data, and inhibitory IC50 values for these nonspirocyclic 2'-substituted (SO2R) phenylhydantoins are in accord with what is expected for spirocyclic hydantoins and comparable to those of sorbinil.

  DOI：

  10.1021/jm00126a011
• 作为产物：
  描述：

  (5-Fluoro-2-methylsulfanylphenyl)methanol 在 manganese(IV) oxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 5-<5-fluoro-2-(methylthio)phenyl>imidazolidine-2,4-dione
  参考文献：
  名称：

  Rotationally restricted mimics of rigid molecules: nonspirocyclic hydantoin aldose reductase inhibitors

  摘要：

  Sorbinil (1), a spirocyclic hydantoin, is a potent inhibitor of the enzyme aldose reductase. Simulation of the rigid spirocyclic ring orientation found in sorbinil was achieved with nonspirocyclic 5-[5'-chloro-2'-(alkylsulfonyl)-phenyl]hydantoins and 5-[5'-chloro-2'-[(N-alkylamino)sulfonyl]phenyl]hydantoins. The 2'-substituent (SO2R) was sufficiently large to hinder rotation of the hydantoin ring, forcing an orientation similar to that of a spirocyclic hydantoin. Calculated conformational preference, X-ray data, and inhibitory IC50 values for these nonspirocyclic 2'-substituted (SO2R) phenylhydantoins are in accord with what is expected for spirocyclic hydantoins and comparable to those of sorbinil.

  DOI：

  10.1021/jm00126a011