1-acetyl-3-phenyl-2,4-imidazolidinedione | 76144-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-acetyl-3-phenyl-2,4-imidazolidinedione
• 英文别名: 1-acetyl-3-phenyl-imidazolidine-2,4-dione；1-Acetyl-3-phenyl-imidazolidin-2,4-dion；1-acetyl-3-phenyl-imidazole-2,4-dione；1-phenyl-3-acetylhydantoin；1-acetyl-3-phenylimidazolidine-2,4-dione
• CAS: 76144-70-2
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: FKJCEETZQTXSHE-UHFFFAOYSA-N

物化性质

• 沸点：
  333.4±25.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)
• 溶解度：
  >32.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硫代异氰酸苯酯 、 N-乙酰甘氨酸 在 silver trifluoroacetate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以58%的产率得到1-acetyl-3-phenyl-2,4-imidazolidinedione
  参考文献：
  名称：

  Silver(I) Ion-mediated Desulfurization-Cyclization of Isothiocyanates with Several Hydroxy Acids and N-Substituted Amino Acids

  摘要：

  The title reaction of 2-hydroxy-2-methylpropionic acid with phenyl isothiocyanate gave 5,5-dimethyl-3-phenyl-2,4-oxazolidinedione. The structure was determined by X-Ray crystal analysis, and the reaction pathway was estimated. The reactions of other 2-hydroxylacids with isothiocyanates also gave some 2,4-oxazolidinediones in good yields. 3-Hydroxybutyric acid, salicylic acid, 3-hydroxy-2-naphthoic acid, and 3-hydroxypyridine-2-carboxylic acid afforded the corresponding cyclic products through the desulfurization-cyclization with isothiocyanate, respectively. N-Substituted amino acids gave several imidazolidine-2,4-diones in the same way.

  DOI：

  10.3987/com-99-8675

文献信息

• Ortin et al., Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, 1958, vol. 54, p. 69,78
  作者：Ortin et al.

  DOI：——

  日期：——
• Silver(I) Ion-mediated Desulfurization-Cyclization of Isothiocyanates with Several Hydroxy Acids and N-Substituted Amino Acids
  作者：Isao Shibuya、Midori Goto、Masao Shimizu、Masaru Yanagisawa、Yuasuo Gama

  DOI：10.3987/com-99-8675

  日期：——

  The title reaction of 2-hydroxy-2-methylpropionic acid with phenyl isothiocyanate gave 5,5-dimethyl-3-phenyl-2,4-oxazolidinedione. The structure was determined by X-Ray crystal analysis, and the reaction pathway was estimated. The reactions of other 2-hydroxylacids with isothiocyanates also gave some 2,4-oxazolidinediones in good yields. 3-Hydroxybutyric acid, salicylic acid, 3-hydroxy-2-naphthoic acid, and 3-hydroxypyridine-2-carboxylic acid afforded the corresponding cyclic products through the desulfurization-cyclization with isothiocyanate, respectively. N-Substituted amino acids gave several imidazolidine-2,4-diones in the same way.