2-phenyl-3-[2-(N,N-dimethylamino)ethyl]-1,3-thiazolidin-4-one | 141956-26-5

• 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: 2-phenyl-3-[2-(N,N-dimethylamino)ethyl]-1,3-thiazolidin-4-one
• 英文别名: 3-(2-dimethylamino-ethyl)-2-phenyl-thiazolidin-4-one；3-(2-Dimethylamino-aethyl)-2-phenyl-thiazolidin-4-on；3-[2-(Dimethylamino)ethyl]-2-phenyl-1,3-thiazolidin-4-one
• CAS: 141956-26-5
• 化学式: C₁₃H₁₈N₂OS
• 分子量: 250.365
• InChiKey: LRWVCOTXBXWRAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 以 苯 为溶剂， 生成 2-phenyl-3-[2-(N,N-dimethylamino)ethyl]-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Thiazolidin-4-one formation. Mechanistic and synthetic aspects of the reaction of imines and mercaptoacetic acid under microwave and conventional heating

  摘要：

  在苯中对苄叉苯胺和巯基乙酸的混合物进行微波辐射，可以高产率（65-90%）合成1,3-噻唑烷-4-酮，而采用传统方法在回流温度下进行相同反应，则需要更长的时间并且产率较低（25-69%）。这种差异似乎是由于传统反应过程中产生了一些中间体和副产物。基于1H NMR研究，假设在苯和DMF中分别存在两种不同的机制，促成噻唑烷-4-酮体系的形成。

  DOI：

  10.1039/b405400h

文献信息

• Synthesis and antihistaminic activity of some thiazolidin-4-ones
  作者：M. Vittoria Diurno、Orazio Mazzoni、Eugenio Piscopo、Antonio Calignano、Federico Giordano、Adele Bolognese

  DOI：10.1021/jm00093a025

  日期：1992.7

  A new series of 2-(4- and 3-substituted phenyl)-3-[3-(N,N-dimethylamino) propyl]-1,3-thiazolidin-4-ones were synthesized, characterized, and evaluated for their ability to inhibit the contractions induced by histamine on guinea pig ileum. The measurement of pA2 values suggested that the reported compounds showed H1-antagonism. The more active compounds 5, 9, and 13 exhibited activity close to that

  合成了一系列新的2-（4-和3-取代的苯基）-3- [3-（N，N-二甲基氨基）丙基] -1,3-噻唑烷丁-4-酮，表征并评价了它们的能力抑制组胺诱导的豚鼠回肠收缩。pA2值的测量表明所报道的化合物表现出H1拮抗作用。活性更高的化合物5、9和13表现出的活性接近美吡拉敏。
• The Preparation of 4-Thiazolidones. III. The Reaction of Methyl Thioglycolate with Benzylidene Dialkylaminoalkylamines
  作者：Alexander R. Surrey

  DOI：10.1021/ja01177a048

  日期：1949.9
• Thiazolidin-4-one formation. Mechanistic and synthetic aspects of the reaction of imines and mercaptoacetic acid under microwave and conventional heating
  作者：Adele Bolognese、Gaetano Correale、Michele Manfra、Antonio Lavecchia、Ettore Novellino、Vincenzo Barone

  DOI：10.1039/b405400h

  日期：——

  Microwave irradiation of a mixture of benzylidene-anilines and mercaptoacetic acid in benzene gives 1,3-thiazolidin-4-ones in very high yield (65–90%), whereas the same reaction performed through using the conventional method, at reflux temperature, requires a much longer time and gives a much lower yield (25–69%). This difference seems to be due to some intermediates and by-products formed during the conventional reaction. On the basis of 1H NMR studies, two different mechanisms, acting in benzene and in DMF, respectively, have been hypothesized for the thiazolidin-4-one system formation.

  在苯中对苄叉苯胺和巯基乙酸的混合物进行微波辐射，可以高产率（65-90%）合成1,3-噻唑烷-4-酮，而采用传统方法在回流温度下进行相同反应，则需要更长的时间并且产率较低（25-69%）。这种差异似乎是由于传统反应过程中产生了一些中间体和副产物。基于1H NMR研究，假设在苯和DMF中分别存在两种不同的机制，促成噻唑烷-4-酮体系的形成。