2-isopropyl-1,2-dimethyl-5-oxo-4-(p-tolyl)-2,5-dihydro-1H-imidazole 3-oxide | 1337877-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-isopropyl-1,2-dimethyl-5-oxo-4-(p-tolyl)-2,5-dihydro-1H-imidazole 3-oxide
• 英文别名: rac-2-isopropyl-2,3-dimethyl-1-oxy-5-p-tolyl-2,3-dihydroimidazol-4-one；2,3-dimethyl-5-(4-methylphenyl)-1-oxido-2-propan-2-ylimidazol-1-ium-4-one
• CAS: 1337877-98-1
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: MJFISAWBEBBMQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-isopropyl-1,2-dimethyl-5-oxo-4-(p-tolyl)-2,5-dihydro-1H-imidazole 3-oxide 在 lithium aluminium tetrahydride 、 水 、 sodium sulfate 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 0.5h， 生成 rac-(2R,5S)-1-hydroxy-2-isopropyl-2,3-dimethyl-5-p-tolylimidazolidin-4-one
  参考文献：
  名称：

  Totally diastereoselective addition of aryl Grignard reagents to the nitrone-based chiral glycine equivalent MiPNO

  摘要：

  The reaction of the chiral nitrone MiPNO (2-isopropyl-2,3-dimethyl-1-oxy-2,3-dihydro-imidazol-4-one) with Grignard reagents is totally diastereoselective. Using simple and functionalized arylmagnesium reagents, enantiopure hydroxylamines were obtained in fair to good yields, which in turn could be easily transformed into new chiral ketonitrones. The preparation of enantiopure L-phenylglycine derivatives is also described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.022
• 作为产物：
  描述：

  对甲苯基溴化镁 在 manganese(IV) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-isopropyl-1,2-dimethyl-5-oxo-4-(p-tolyl)-2,5-dihydro-1H-imidazole 3-oxide
  参考文献：
  名称：

  Totally diastereoselective addition of aryl Grignard reagents to the nitrone-based chiral glycine equivalent MiPNO

  摘要：

  The reaction of the chiral nitrone MiPNO (2-isopropyl-2,3-dimethyl-1-oxy-2,3-dihydro-imidazol-4-one) with Grignard reagents is totally diastereoselective. Using simple and functionalized arylmagnesium reagents, enantiopure hydroxylamines were obtained in fair to good yields, which in turn could be easily transformed into new chiral ketonitrones. The preparation of enantiopure L-phenylglycine derivatives is also described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.022

文献信息

• Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization
  作者：Marta Carbó López、Guy Royal、Christian Philouze、Pierre Y. Chavant、Véronique Blandin

  DOI：10.1002/ejoc.201402324

  日期：2014.8

  co-catalytic system. In some cases, rapid oxidation to benzaldehyde was accomplished at room temperature under an atmospheric O2 pressure. Moreover, atroposelective desymmetrization was achieved during the aerobic oxidation of a diol catalyzed by an enantiopure imidazolidinone nitroxide. Finally, the electrochemical behavior of the new hydroxylamines and nitroxides was investigated by cyclic voltammetry

  基于 imidazolidin-4-one 骨架的新型手性氮氧化物和相应的羟胺，已通过简单的反应顺序从环状硝酮制备。它们被评估为使用不同助催化剂进行苯甲醇有氧氧化的催化剂。咪唑烷酮氮氧化物和羟胺都被证明可以催化反应，环取代基的影响取决于助催化体系。在某些情况下，在室温和大气 O2 压力下快速氧化为苯甲醛。此外，在对映体纯咪唑烷酮硝基氧催化的二醇有氧氧化过程中实现了阻生选择性去对称化。最后，通过循环伏安法研究了新的羟胺和硝基氧的电化学行为，
• Fast Pd- and Pd/Cu-Catalyzed Direct C–H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α-Amino Esters
  作者：Emilien Demory、Daniel Farran、Benoit Baptiste、Pierre Y. Chavant、Véronique Blandin

  DOI：10.1021/jo301114k

  日期：2012.9.21

  very fast, clean, and high-yielding palladium-catalyzed coupling of a large array of aryl, thienyl, and pyridyl halides with cyclic nitrones, including DMPO. The study of the reaction conditions, scope, and mechanism is presented. Applied to the chiral nitrone MiPNO, this transformation provides a straightforward access to enantiopure α-methyl α-arylglycine esters.

  新戊酸或溴化铜的共催化作用使大量的芳基，噻吩基和吡啶基卤化物与环状硝酮（包括DMPO）非常快速，清洁和高产率地由钯催化偶联。介绍了反应条件，范围和机理的研究。应用于手性硝酮MiPNO，这种转化可以直接获得对映纯α-甲基α-芳基甘氨酸酯。