5,5-dimethyl-3-(o-tolyl)-2-thioxo-4-oxazolidinone | 144267-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5-dimethyl-3-(o-tolyl)-2-thioxo-4-oxazolidinone
• 英文别名: N-(o-tolyl)-5,5-dimethyl-2-thioxo-4-oxazolidinone；5,5-Dimethyl-3-(2-methylphenyl)-2-sulfanylidene-1,3-oxazolidin-4-one
• CAS: 144267-91-4；151797-47-6；151797-48-7；1013919-40-8；1013919-41-9
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: SZCDMJMZHWABQB-UHFFFAOYSA-N

物化性质

• 沸点：
  298.5±33.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-萘胺 在 lead(II) nitrate 、 sodium 作用下， 以 ammonium hydroxide 、 sodium hydroxide 、 甲苯 为溶剂， 反应 4.0h， 生成 5,5-dimethyl-3-(o-tolyl)-2-thioxo-4-oxazolidinone
  参考文献：
  名称：

  1H and13C NMR studies on 3-aryl-2-thioxo-4-oxazolidinones and 3-arylrhodanines

  摘要：

  Abstract3‐Aryl‐2‐thioxo‐4‐oxazolidinones and 3‐arylrhodanines have been studied for magnetic non‐equivalence of diastereotopically related proton and 13C nuclei in rotational isomers, and for steric interactions between the aryl and heterocyclic moieties of these compounds. For the majority of rotational isomers the barriers to internal rotation about the aryl CN bond were >100 kJ mol−1, due to the steric bulk of the thiocarbonyl group. Chemical isolation of several of the diastereomers was achieved. The enhanced steric effect and the difference in the electronic effect of the sulphur atom in relation to the oxygen atom appeared to have no influence on the small chemical shift differences of the rotational isomers, detected for some 1H and some 13C nuclei.

  DOI：

  10.1002/omr.1270210906

文献信息

• Synthesis and NMR studies of chiral 4-oxazolidinones and rhodanines
  作者：Í. Dog̃an、T. Burgemeister、S. Íçli、A. Mannschreck

  DOI：10.1016/s0040-4020(01)88256-9

  日期：1992.1

  Sterically hindered N-(o-tolyl) and N-(o-chlorophenyl) substituted 2-thioxo-4-oxazolidinones 1 and-thiazolidinones (rhodanines) 2 forming enantiomers by partial rotation around the C-N bond are synthesized. Their chirality is proven by the presence of diastereotopic protons (or carbon atoms) detected by H-1 or C-13 NMR (1c, 2c). In the presence of (S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol as an auxiliary the enantiomers showed H-1 shift differences of 0.01 ppm for otherwise isochronous nuclei.
• 1H and13C NMR studies on 3-aryl-2-thioxo-4-oxazolidinones and 3-arylrhodanines
  作者：Zihni Aksaç、Esat Pinar、Sîddîk Içli

  DOI：10.1002/omr.1270210906

  日期：1983.9

  Abstract3‐Aryl‐2‐thioxo‐4‐oxazolidinones and 3‐arylrhodanines have been studied for magnetic non‐equivalence of diastereotopically related proton and 13C nuclei in rotational isomers, and for steric interactions between the aryl and heterocyclic moieties of these compounds. For the majority of rotational isomers the barriers to internal rotation about the aryl CN bond were >100 kJ mol−1, due to the steric bulk of the thiocarbonyl group. Chemical isolation of several of the diastereomers was achieved. The enhanced steric effect and the difference in the electronic effect of the sulphur atom in relation to the oxygen atom appeared to have no influence on the small chemical shift differences of the rotational isomers, detected for some 1H and some 13C nuclei.