3,5-二甲基-5-苯基-2,4-咪唑烷二酮 | 201607-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3,5-二甲基-5-苯基-2,4-咪唑烷二酮
• 英文名称: (R)-3,5-dimethyl-5-phenylimidazolidine-2,4-dione
• 英文别名: (5S)-3,5-Dimethyl-5-phenylimidazolidine-2,4-dione；(5S)-3,5-dimethyl-5-phenylimidazolidine-2,4-dione
• CAS: 201607-11-6
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: ONMINFICGHKHPM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-二甲基-5-苯基-2,4-咪唑烷二酮 在 sodium hydroxide 作用下， 反应 65.0h， 以92%的产率得到(alphaR)-(9CI)-α-氨基-α-甲基-苯乙酸
  参考文献：
  名称：

  伪麻黄碱指示的α-氨基酸衍生物的不对称α-芳基化作用

  摘要：

  可用的α-氨基酸在与连接到假麻黄碱的N'-芳基尿素衍生物的碱作为手性助剂的处理下，以对映选择性的方式在其α位进行芳基化。原位甲硅烷基化和烯醇化诱导N'-芳基向非对映选择性迁移至氨基酸的α位置，随后闭环至乙内酰脲，同时伴随着可回收助剂的爆炸。乙内酰脲产物的水解提供了季氨基酸的衍生物。芳基化避免使用重金属添加剂，并且成功地用于一系列氨基酸和具有不同电子特性的芳基环。

  DOI：

  10.1002/anie.201502569
• 作为产物：
  描述：

  3,5-二甲基-5-苯基咪唑烷-2,4-二酮 生成 (R)-3-methyl-5-methyl-5-phenylimidazolidine-2,4-dione 、 3,5-二甲基-5-苯基-2,4-咪唑烷二酮
  参考文献：
  名称：

  Investigation of a broadly applicable chiral selector used in enantioselective chromatography (Whelk-O 1) as a chiral solvating agent for NMR determination of enantiomeric composition

  摘要：

  A chiral solvating agent (CSA) based on the chiral selector used in the Whelk-O I chiral stationary phase (CSP) was prepared and its scope evaluated. This chiral selector possesses a cleft flanked with aromatic groups and produces upfield chemical shifts for analytes. which are held in this cleft. The enantiomers of each of the Whelk-O I resolvable analytes surveyed show non-equivalent H-1 NMR spectra at room temperature with the addition of only 0.5 equiv of the CSA. Similar non-equivalence is sometimes noted for enantiomers, which do not resolve on this CSP. In such cases, it is apparent that a hydrogen bond acceptor is required and higher CSA to substrate ratios and/or lower temperatures may be needed if adequate resolution of enantiomeric signals is to be obtained. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.032

文献信息

• Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives
  作者：Rachel C. Atkinson、Fernando Fernández-Nieto、Josep Mas Roselló、Jonathan Clayden

  DOI：10.1002/anie.201502569

  日期：2015.7.27

  Available α‐amino acids undergo arylation at their α position in an enantioselective manner on treatment with base of N′‐aryl urea derivatives ligated to pseudoephedrine as a chiral auxiliary. In situ silylation and enolization induces diastereoselective migration of the N′‐aryl group to the α position of the amino acid, followed by ring closure to a hydantoin with concomitant explulsion of the recyclable

  可用的α-氨基酸在与连接到假麻黄碱的N'-芳基尿素衍生物的碱作为手性助剂的处理下，以对映选择性的方式在其α位进行芳基化。原位甲硅烷基化和烯醇化诱导N'-芳基向非对映选择性迁移至氨基酸的α位置，随后闭环至乙内酰脲，同时伴随着可回收助剂的爆炸。乙内酰脲产物的水解提供了季氨基酸的衍生物。芳基化避免使用重金属添加剂，并且成功地用于一系列氨基酸和具有不同电子特性的芳基环。
• Investigation of a broadly applicable chiral selector used in enantioselective chromatography (Whelk-O 1) as a chiral solvating agent for NMR determination of enantiomeric composition
  作者：Michael E. Koscho、William H. Pirkle

  DOI：10.1016/j.tetasy.2005.08.032

  日期：2005.10

  A chiral solvating agent (CSA) based on the chiral selector used in the Whelk-O I chiral stationary phase (CSP) was prepared and its scope evaluated. This chiral selector possesses a cleft flanked with aromatic groups and produces upfield chemical shifts for analytes. which are held in this cleft. The enantiomers of each of the Whelk-O I resolvable analytes surveyed show non-equivalent H-1 NMR spectra at room temperature with the addition of only 0.5 equiv of the CSA. Similar non-equivalence is sometimes noted for enantiomers, which do not resolve on this CSP. In such cases, it is apparent that a hydrogen bond acceptor is required and higher CSA to substrate ratios and/or lower temperatures may be needed if adequate resolution of enantiomeric signals is to be obtained. (c) 2005 Elsevier Ltd. All rights reserved.