(S)-(+)-5-(4-methylphenyl)-5-methylhydantoin | 142777-71-7

• 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-(4-methylphenyl)-5-methylhydantoin
• 英文别名: (5S)-5-methyl-5-(4-methylphenyl)imidazolidine-2,4-dione
• CAS: 142777-71-7
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: RTMDEHNRMKFSML-NSHDSACASA-N

物化性质

• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-5-(4-methylphenyl)-5-methylhydantoin 在 sodium hydroxide 、 potassium permanganate 作用下， 反应 3.0h， 以65%的产率得到(S)-(+)-5-(4-carboxyphenyl)-5-methylhydantoin
  参考文献：
  名称：

  An efficient access to the enantiomers of α-methyl-4-carboxyphenylglycine via a hydantoin route using a practical variant of preferential crysallization AS3PC (Auto Seeded Programmed Polythermic Preferential Crystallization)11

  摘要：

  The enantiomers are obtained in preparative amounts without a resolving agent via the following sequence: hydantoin synthesis, resolution by entrainment, and ring cleavage by means of hydrolysis in basic conditions. The new variant of preferential crystallization (AS3PC), implemented without using seeds, shows good reproducibility and yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00349-2
• 作为产物：
  描述：

  5-甲基-5-（4-甲基苯基）咪唑烷-2,4-二酮 生成 (S)-(+)-5-(4-methylphenyl)-5-methylhydantoin
  参考文献：
  名称：

  An efficient access to the enantiomers of α-methyl-4-carboxyphenylglycine via a hydantoin route using a practical variant of preferential crysallization AS3PC (Auto Seeded Programmed Polythermic Preferential Crystallization)11

  摘要：

  The enantiomers are obtained in preparative amounts without a resolving agent via the following sequence: hydantoin synthesis, resolution by entrainment, and ring cleavage by means of hydrolysis in basic conditions. The new variant of preferential crystallization (AS3PC), implemented without using seeds, shows good reproducibility and yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00349-2

文献信息

• Design and scalable synthesis of new chiral selectors. Part 1: Synthesis and characterization of a new constrained cyclopeptide from unnatural bulky amino acids
  作者：Laurent Ferron、Frédéric Guillen、Servane Coste、Gérard Coquerel、Pascal Cardinaël、Joël Schwartz、Jean-Marc Paris、Jean-Christophe Plaquevent

  DOI：10.1016/j.tet.2011.06.032

  日期：2011.8

  We describe the conception, synthesis, and characterization of a novel cyclopeptide designed for chiral recognition. The asymmetric units are built from an unnatural amino acid in the series of α-aryl-α-methyl glycine. Modifications of standard methods of peptide synthesis are described in order to improve yields and purities when applied to hindered amino acids. First set of experiments about host–guest

  我们描述了为手性识别设计的新型环肽的概念，合成和表征。不对称单元由一系列α-芳基-α-甲基甘氨酸中的非天然氨基酸构成。描述了对肽合成的标准方法的修改，以便在应用于受阻氨基酸时提高产量和纯度。公开了关于获得的环肽的宿主-客体能力的第一组实验。
• An efficient access to the enantiomers of α-methyl-4-carboxyphenylglycine via a hydantoin route using a practical variant of preferential crysallization AS3PC (Auto Seeded Programmed Polythermic Preferential Crystallization)11
  作者：E. Ndzié、P. Cardinael、A.-R. Schoofs、G. Coquerel

  DOI：10.1016/s0957-4166(97)00349-2

  日期：1997.9

  The enantiomers are obtained in preparative amounts without a resolving agent via the following sequence: hydantoin synthesis, resolution by entrainment, and ring cleavage by means of hydrolysis in basic conditions. The new variant of preferential crystallization (AS3PC), implemented without using seeds, shows good reproducibility and yield. (C) 1997 Elsevier Science Ltd.