3-(o-bromophenyl)rhodanine | 56676-48-3

• 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: 3-(o-bromophenyl)rhodanine
• 英文别名: 3-(2-bromo-phenyl)-2-thioxo-thiazolidin-4-one；3-(2-Brom-phenyl)-2-thioxo-thiazolidin-4-on；4-Thiazolidinone, 3-(2-bromophenyl)-2-thioxo-；3-(2-bromophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 56676-48-3
• 化学式: C₉H₆BrNOS₂
• 分子量: 288.189
• InChiKey: FISNJKOEQSRSLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-bromo-2-isothiocyanatobenzene 、 巯基乙酸乙酯 在 sodium 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以60%的产率得到3-(o-bromophenyl)rhodanine
  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

• 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.
• Axially chiral N-(o-aryl)-2-thioxo-oxazolidine-4-one and rhodanine derivatives: enantiomeric separation and determination of racemization barriers
  作者：Esra Müjde Yılmaz、İlknur Doğan

  DOI：10.1016/j.tetasy.2008.09.001

  日期：2008.9

  Axially chiral 5,5-dimethyl-3-(o-aryl)rhodanine, 3-(o-aryl)rhodanine and 5,5-dimethyl-3-(o-aryl)-2-thioxo-4-oxazolidinone derivatives have been synthesized as racemates and the energy barriers to enantiomerization have been determined by dynamic H-1 NMR or by following the thermal equilibration of the separated enantiomers using chiral HPLC. The barriers to rotation about the N-sp2-C-aryl single bond were found to be 82-129 kJ/mol. The racemization barriers in these compounds are affected by the size of the ortho-substituent on the aryl ring. The magnitude of the barriers was found to change linearly with the van der Waals radii of the ortho-halogen substituents. (C) 2008 Elsevier Ltd. All Fights reserved.

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