N-(o-tolyl)-5,5-dimethylrhodanine | 144267-94-7

• 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: N-(o-tolyl)-5,5-dimethylrhodanine
• 英文别名: 5,5-Dimethyl-3-(2-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one；5,5-dimethyl-3-(2-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 144267-94-7
• 化学式: C₁₂H₁₃NOS₂
• 分子量: 251.373
• InChiKey: JOOGRTBXMHDCDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(o-tolyl)-5,5-dimethylrhodanine 在 溴 、 溶剂黄146 作用下， 以56%的产率得到5,5-Dimethyl-3-(2-methylphenyl)-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Chiral <i>N</i>-(<i>o</i>-aryl)-thiazolidinediones: synthesis from rhodanines and investigation on rotational enantiomers by NMR spectroscopy

  摘要：

  Sterically hindered N-(o-aryl)-rhodanines (a) (N-(o-aryl)-2-thioxo-4-thiazolidinones) have been synthesized and the N-(o-tolyl) and N-(o-chlorophenyl) derivatives have been converted to their dioxo analogs (b) (N-(o-aryl)-2,4-thiazolidine-diones). The chirality of the compounds in their conformational ground states was proved by detection of the diastereotopic protons or methyl groups at C-5 of the heteroring using H-1 and C-13 NMR spectroscopy. In the presence of the optically active auxiliary (S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol the enantiomers of the racemic mixtures formed diastereomeric association complexes via H-bonding.

  DOI：

  10.1139/cjc-76-3-254
• 作为产物：
  描述：

  o-tolyl-dithiocarbamic acid; ammonium salt 、 α-bromoisobutyric acid potassium salt 在 氢氧化钾 作用下， 生成 N-(o-tolyl)-5,5-dimethylrhodanine
  参考文献：
  名称：

  Synthesis and NMR studies of chiral 4-oxazolidinones and rhodanines

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)88256-9

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.
• Chiral &lt;i&gt;N&lt;/i&gt;-(&lt;i&gt;o&lt;/i&gt;-aryl)-thiazolidinediones: synthesis from rhodanines and investigation on rotational enantiomers by NMR spectroscopy
  作者：Mehmet Karatas、Serap Koni、Ilknur Dogan

  DOI：10.1139/cjc-76-3-254

  日期：——

  Sterically hindered N-(o-aryl)-rhodanines (a) (N-(o-aryl)-2-thioxo-4-thiazolidinones) have been synthesized and the N-(o-tolyl) and N-(o-chlorophenyl) derivatives have been converted to their dioxo analogs (b) (N-(o-aryl)-2,4-thiazolidine-diones). The chirality of the compounds in their conformational ground states was proved by detection of the diastereotopic protons or methyl groups at C-5 of the heteroring using H-1 and C-13 NMR spectroscopy. In the presence of the optically active auxiliary (S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol the enantiomers of the racemic mixtures formed diastereomeric association complexes via H-bonding.