3,5,5-triphenyl-2-thiohydantoin | 52460-98-7

• 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: 3,5,5-triphenyl-2-thiohydantoin
• 英文别名: 3,5,5-triphenyl-2-thioxo-imidazolidin-4-one；3,5,5-Triphenyl-2-thioxo-4-imidazolidinone；3,5,5-triphenyl-2-sulfanylideneimidazolidin-4-one
• CAS: 52460-98-7
• 化学式: C₂₁H₁₆N₂OS
• 分子量: 344.437
• InChiKey: VYCBHDCXQUZIJV-UHFFFAOYSA-N

物化性质

• 熔点：
  255-256 °C(Solv: ethanol (64-17-5))
• 沸点：
  482.6±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5,5-triphenyl-2-thiohydantoin 生成 2-Methylthio-1,4,4-triphenyl-2-imidazolin-5-on
  参考文献：
  名称：

  On the Formation and Reactions of the Substituted Thiazolidones. IV

  摘要：

  DOI：

  10.1021/ja01303a050
• 作为产物：
  描述：

  苯甲醛 在 盐酸 、 盐酸硫胺 作用下， 反应 0.5h， 生成 3,5,5-triphenyl-2-thiohydantoin
  参考文献：
  名称：

  某些有趣的杂环衍生物作为杀虫剂的高效绿色合成和计算化学研究

  摘要：

  一系列5,5- diarylhydantoin（大仑丁）的3，4，和7，咪唑1，2，5，6，8，和9，噻唑10 - 12，triazinthione 13，15，16，和17，和噻二嗪14使用研磨技术和常规热方法，通过芳香醛，维生素B1和氮亲核试剂（例如尿素，硫脲和硫代氨基脲）的一锅式逐步反应，绿色合成了包含各种疏水基团的衍生物。这种合成的化合物具有有效的杀虫活性。例如，化合物4，6，和17表现出对两者的最高杀虫活性小菜蛾和棉铃虫最小抑菌浓度为500μg/ mL，LD50活性为50μg/ mL。然后将密度泛函理论应用于探索这些化合物的结构和电子特性。所有合成的化合物均已根据其元素分析和光谱数据进行了表征。

  DOI：

  10.1002/jhet.3308

文献信息

• 5,5-Diaryl-2-thiohydantoins and 5,5-diaryl N3-substituted 2-thiohydantoins as potential hypolipidemic agents
  作者：J. Ellsworth Tompkins

  DOI：10.1021/jm00155a042

  日期：1986.5

  A series of 5,5-diaryl-2-thiohydantoins and 5,5-diaryl-N3-substituted-2-thiohydantoins related to 5,5-diphenyl-2-thiohydantoin (DPTH) were investigated as potential hypolipidemic agents with the goal of increased potency over DPTH itself. In the 5,5-diaryl class, the best results were obtained by substituting two pyridyl rings for the phenyl rings found in DPTH. The resulting compound, 5,5-bis(2-p

  为了研究潜在的降血脂药，研究了一系列与5,5-二苯基-2-硫代乙内酰脲（DPTH）有关的5,5-二芳基-2-硫代乙内酰脲和5,5-二芳基-N3-取代的-2-硫代乙内酰脲。增强了DPTH本身的效能。在5,5-二芳基类别中，最好的结果是用两个吡啶环取代DPTH中的苯环。所得化合物5,5-双（2-吡啶基）-2-硫代乙内酰脲DPYTH（5）在降低肝脏胆固醇值方面比DPTH略好。DPYTH（5）的进一步修改正在进行中，并将成为未来报告的主题。在N3氮取代的系列中，一种化合物5,5-二苯基-N3-正丁基-2-硫代乙内酰脲（DPBTH）（7）在初次筛选时显示出希望，但在剂量反应研究中进行分析时，
• Oxidation of Thioamides to Amides with Tetrachloro- and Tetrabromoglycolurils
  作者：I. Boudebouz、S. Arrous、I. V. Parunov

  DOI：10.1134/s1070428019120108

  日期：2019.12

  Tetrabromo- and tetrachloroglycolurils have been shown to act as good oxidants capable of converting thioamides to the corresponding amides. This approach offers such advantages as good yields (81-99%), short reaction times (10-25 min), simple workup procedure, and environmental safety.
• Synthesis of Hydantoins, Thiohydantoins, and Glycocyamidines Under Solvent-Free Conditions
  作者：Imran Ali Hashmi、Afshan Aslam、Syed Kashif Ali、Viqar-uddin Ahmed、Firdous Imran Ali

  DOI：10.1080/00397910903320662

  日期：2010.8.31

  Hydantoins, thiohydantoins, and glycocyamidines have been prepared in moderate to excellent yields at room temperature under solvent-free conditions. 3N-amino and carboamide derivatives of hydantoin (7-8) were prepared in single step by condensing benzil with semicarbazide and biuret respectively.
• Substituted 2-Thioxoimidazolidin-4-ones and Imidazolidine-2,4-diones as Fatty Acid Amide Hydrolase Inhibitors Templates
  作者：Giulio G. Muccioli、Nicola Fazio、Gerhard K. E. Scriba、Wolfgang Poppitz、Fabio Cannata、Jacques H. Poupaert、Johan Wouters、Didier M. Lambert

  DOI：10.1021/jm050977k

  日期：2006.1.1

  The demonstration of the essential role of fatty acid amide hydrolase (FAAH) in hydrolyzing endogenous bioactive fatty acid derivatives has launched the quest for the discovery of inhibitors for this enzyme. Along this line, a set of 58 imidazolidine-2,4-dione and 2-thioxoirnidazolidin-4-one derivatives was evaluated as FAAH inhibitors. Among these compounds, 3-substituted 5,5'-diplietiylimidazolidine-2,4-dione and 3-substituted 5,5'-diphenyl-2-thioxoimidazolidin-4-one derivatives were previously described as CB, cannabinoid receptor ligands. In the present study, we synthesized several derivatives exhibiting interesting FAAH inhibitory activity and devoid of affinity for the CB, and CB, cannabinoid receptors. For instance, 3-heptyl-5,5'-diphenylimidazolidine-2,4-dione (14) and 5.5'-diphenyl-3-tetradecyl-2-thioxo-imidazolidin-4-one (46) showed pI(50) values of 5.12 and 5.94, respectively. In conclusion, it appears that even though several 3-substituted 5,5'-diphenyl-2-thioxoimidazolidin-4-one and 3-substituted 5.5'-diphenylimidazolidine-2,4-dione derivatives have been previously shown to behave as CB, cannabinoid receptor ligands, appropriate substitutions of these templates can result in FAAH inhibitors devoid of affinity for the cannabinoid receptors.
• Broan, Christopher J.; Butler, Anthony R.; Reed, David, Journal of the Chemical Society. Perkin transactions II, 1989, p. 731 - 740
  作者：Broan, Christopher J.、Butler, Anthony R.、Reed, David、Sadler, Ian H.

  DOI：——

  日期：——