(S)-5-benzyl-3-(4-chlorophenyl)-2-thioxoimidazolidin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-5-benzyl-3-(4-chlorophenyl)-2-thioxoimidazolidin-4-one
• 英文别名: 5-benzyl-3-(4-chlorophenyl)-2-thioxoimidazolidin-4-one；(5S)-5-benzyl-3-(4-chlorophenyl)-2-sulfanylideneimidazolidin-4-one
• 化学式: C₁₆H₁₃ClN₂OS
• 分子量: 316.811
• InChiKey: LLOAJEWGFPKUDH-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以0.12 g的产率得到(S)-5-benzyl-3-(4-chlorophenyl)-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins

  摘要：

  A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.041

文献信息

• New functionalized 8-hydroxyquinoline-5-sulfonic acid mesoporous silica (HQS-SBA-15) as an efficient catalyst for the synthesis of 2-thiohydantoin derivatives
  作者：Vaezeh Fathi Vavsari、Ghodsi Mohammadi Ziarani、Saeed Balalaie、Arezoo Latifi、Mehdi Karimi、Alireza Badiei

  DOI：10.1016/j.tet.2016.07.034

  日期：2016.9

  Mesoporous silica SBA-15 functionalized with 8-hydroxyquinoline-5-sulfonic acid (HQS-SBA-15) was used as a new recyclable nanocatalyst for the one-pot synthesis of 2-thiohydantoin derivatives under solvent-free conditions. The catalyst exhibited excellent recyclability at least for 3 times with a high catalytic activity.

  使用8-羟基喹啉-5-磺酸（HQS-SBA-15）功能化的介孔二氧化硅SBA-15作为一种新型可回收纳米催化剂，用于在无溶剂条件下一锅合成2-硫代乙内酰脲衍生物。该催化剂至少具有3次优异的可再循环性，并具有高催化活性。
• Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins
  作者：Yu Chen、Li Su、Xinying Yang、Wenyan Pan、Hao Fang

  DOI：10.1016/j.tet.2015.10.041

  日期：2015.12

  A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature. (C) 2015 Elsevier Ltd. All rights reserved.