3-(2-氯苯基)-1,3-噻唑烷-2,4-二酮 | 73219-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3-(2-氯苯基)-1,3-噻唑烷-2,4-二酮
• 英文名称: 3-(2-chloro-phenyl)-thiazolidine-2,4-dione
• 英文别名: 3-(2-Chlorophenyl)-1,3-thiazolidine-2,4-dione
• CAS: 73219-83-7
• 化学式: C₉H₆ClNO₂S
• mdl: MFCD03828114
• 分子量: 227.671
• InChiKey: HSIPWRGYFQUTDR-UHFFFAOYSA-N

物化性质

• 沸点：
  344.5±44.0 °C(Predicted)
• 密度：
  1.534±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-氯苯基)-1,3-噻唑烷-2,4-二酮 在 potassium permanganate 作用下， 以 溶剂黄146 为溶剂， 生成 3-(2-chloro-phenyl)-1,1-dioxo-1λ⁶-thiazolidine-2,4-dione
  参考文献：
  名称：

  Rao,R.P. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1979, vol. 18, p. 377 - 379

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,4-三氯萘 、 巯基乙酸乙酯 在 sodium 作用下， 以 甲苯 为溶剂， 反应 11.0h， 以19%的产率得到3-(2-氯苯基)-1,3-噻唑烷-2,4-二酮
  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

文献信息

• RAO R. P.; SINGH S. R.; ZAIDI N. B.; SINGH B., INDIAN J. CHEM., 1979, B 18, NO 4, 377-379
  作者：RAO R. P.、 SINGH S. R.、 ZAIDI N. B.、 SINGH B.

  DOI：——

  日期：——
• Rao,R.P. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1979, vol. 18, p. 377 - 379
  作者：Rao,R.P. et al.

  DOI：——

  日期：——
• 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.