2-(4-N,N-dimethylaminobenzylidenehydrazono)-1,3-thiazolidin-4-one-5-acetic acid | 6208-40-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4-N,N-dimethylaminobenzylidenehydrazono)-1,3-thiazolidin-4-one-5-acetic acid
• 英文别名: [2-(4-dimethylamino-benzylidenehydrazono)-4-oxo-thiazolidin-5-yl]-acetic acid；2-[(2Z)-2-[[4-(dimethylazaniumyl)phenyl]methylidenehydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl]acetate
• CAS: 6208-40-8
• 化学式: C₁₄H₁₆N₄O₃S
• 分子量: 320.372
• InChiKey: VSTLAGXYQPZCBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  马来酸酐 、 4-(二甲基氨基)苯甲醛缩氨基硫脲 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 0.1h， 以75%的产率得到2-(4-N,N-dimethylaminobenzylidenehydrazono)-1,3-thiazolidin-4-one-5-acetic acid
  参考文献：
  名称：

  Microwave-assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones

  摘要：

  A tandem method for the synthesis of 2-hydrazolyl-4-thiazolidinones (5) from commercially available materials in a 3-component reaction has been developed. The reaction connects aldehydes, thiosemicarbazides, and maleic anhydride, effectively assisted by microwave irradiation. The synthesis of a new type of compound, 2-hydrazolyl-5,5-diphenyl-4-thiazolidinone (7), obtained by treatment of thiosemicarbazone with benzil in basic media is also reported. HOMO/LUMO energies, orbital coefficients, and charge distribution were used to explain the proposed reaction mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.020

文献信息

• Baker’s yeast catalyzed one-pot synthesis of bioactive 2-[benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acids
  作者：Anusaya S. Chavan、Arun S. Kharat、Manisha R. Bhosle、Ramrao A. Mane

  DOI：10.1515/hc-2017-0130

  日期：2018.4.25

  substituted derivatives of 2-hydrazono-4-thiazolidinone-5-acetic acids 4a–j and 6a–g by cyclocondensation of aryl/pyrazolyl aldehyde, thiosemicarbazide and maleic anhydride in acetonitrile in the presence of readily available whole cell biocatalyst, baker’s yeast (Saccharomyces cerevisiae). The reaction is enhanced by ultrasonication.

  摘要 通过芳基/吡唑醛、氨基硫脲和马来酸酐的环缩合反应，开发了一种有效且简单的一锅法，用于合成 2-hydrazono-4-thiazolidinone-5-乙酸 4a-j 和 6a-g 的取代衍生物。在容易获得的全细胞生物催化剂、面包酵母（Saccharomyces cerevisiae）存在下使用乙腈。通过超声处理增强反应。
• Derivatives of 5-Carboxymethylthiazolidine-2,4-dione, a New Group of Antiviral Compounds
  作者：A. Krbavčič、M. Plut、A. Pollak、M. Tišler、M. Likar、P. Schauer

  DOI：10.1021/jm00321a047

  日期：1966.5
• Microwave-assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones
  作者：Cecilia Saiz、Chiara Pizzo、Eduardo Manta、Peter Wipf、S. Graciela Mahler

  DOI：10.1016/j.tetlet.2008.12.020

  日期：2009.2

  A tandem method for the synthesis of 2-hydrazolyl-4-thiazolidinones (5) from commercially available materials in a 3-component reaction has been developed. The reaction connects aldehydes, thiosemicarbazides, and maleic anhydride, effectively assisted by microwave irradiation. The synthesis of a new type of compound, 2-hydrazolyl-5,5-diphenyl-4-thiazolidinone (7), obtained by treatment of thiosemicarbazone with benzil in basic media is also reported. HOMO/LUMO energies, orbital coefficients, and charge distribution were used to explain the proposed reaction mechanism. (C) 2008 Elsevier Ltd. All rights reserved.