5-methyl-3-(4'-dimethylaminophenyl)-2,4-oxazolidinedione

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-methyl-3-(4'-dimethylaminophenyl)-2,4-oxazolidinedione
• 英文别名: 3-[4-(Dimethylamino)phenyl]-5-methyl-1,3-oxazolidine-2,4-dione
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: MSBUJPZAANZWSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乳酸 、 4-二甲氨基苯基硫代异氰酸酯 在 silver trifluoroacetate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以88%的产率得到5-methyl-3-(4'-dimethylaminophenyl)-2,4-oxazolidinedione
  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

• 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.

表征谱图