3-(5-oxo-2-thioxo-1-m-tolyl-imidazolidin-4-yl)propionic acid benzyl ester | 1219279-16-9

• 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: 3-(5-oxo-2-thioxo-1-m-tolyl-imidazolidin-4-yl)propionic acid benzyl ester
• 英文别名: benzyl 3-[(4S)-1-(3-methylphenyl)-5-oxo-2-sulfanylideneimidazolidin-4-yl]propanoate
• CAS: 1219279-16-9
• 化学式: C₂₀H₂₀N₂O₃S
• 分子量: 368.456
• InChiKey: POUXZPXCRUIQJZ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  benzyl (4S)-5-[[4-[(3-methylimidazol-3-ium-1-yl)methyl]phenyl]methylamino]-4-[(3-methylphenyl)carbamothioylamino]-5-oxopentanoate;tetrafluoroborate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-(5-oxo-2-thioxo-1-m-tolyl-imidazolidin-4-yl)propionic acid benzyl ester
  参考文献：
  名称：

  Traceless Approach for the Synthesis of 3,5-Disubstituted Thiohydantoins on Functionalized Ionic-Liquid Support

  摘要：

  A traceless approach for the synthesis of 3,5-disubstituted thiohydantoins on a novel functionalized ionic-liquid support, 5, is described. Acylation of benzylamine functionalized ionic-liquid support with amino acids yielded ionic-liquid-supported amino acids, which reacted with isothiocyanates to afford ionic-liquid-supported thioureas. Following intramolecular cyclization cleavage from the ionic-liquid support by trifluoroacetic acid (TFA), the desired 3,5-disubstituted thiohydantoins were obtained in good yields and purities. The efficiency of this ionic-liquid-phase strategy facilitated isolation and analysis of intermediates and removal of excess reagents and by-products during the reaction process.

  DOI：

  10.1080/00397910903013697

文献信息

• Traceless Approach for the Synthesis of 3,5-Disubstituted Thiohydantoins on Functionalized Ionic-Liquid Support
  作者：Chao Yao、Yandong Zhang、Guolin Zhang、Wenteng Chen、Yongping Yu、Richard A. Houghten

  DOI：10.1080/00397910903013697

  日期：2010.2.12

  A traceless approach for the synthesis of 3,5-disubstituted thiohydantoins on a novel functionalized ionic-liquid support, 5, is described. Acylation of benzylamine functionalized ionic-liquid support with amino acids yielded ionic-liquid-supported amino acids, which reacted with isothiocyanates to afford ionic-liquid-supported thioureas. Following intramolecular cyclization cleavage from the ionic-liquid support by trifluoroacetic acid (TFA), the desired 3,5-disubstituted thiohydantoins were obtained in good yields and purities. The efficiency of this ionic-liquid-phase strategy facilitated isolation and analysis of intermediates and removal of excess reagents and by-products during the reaction process.