4-(4-(dimethylamino)phenyl)-2-isopropyl-1,2-dimethyl-5-oxo-2,5-dihydro-1H-imidazole 3-oxide | 1337877-99-2

• 分子结构分类: 有机化合物
• 英文名称: 4-(4-(dimethylamino)phenyl)-2-isopropyl-1,2-dimethyl-5-oxo-2,5-dihydro-1H-imidazole 3-oxide
• 英文别名: rac-5-(4-dimethylaminophenyl)-2-isopropyl-2,3-dimethyl-1-oxy-2,3-dihydroimidazol-4-one
• CAS: 1337877-99-2
• 化学式: C₁₆H₂₃N₃O₂
• 分子量: 289.378
• InChiKey: YAZAHKNTRAKUNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.62
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  rac-(2R,5R)-5-(4-dimethylaminophenyl)-1-hydroxy-2-isopropyl-2,3-dimethylimidazolidin-4-one 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以100%的产率得到4-(4-(dimethylamino)phenyl)-2-isopropyl-1,2-dimethyl-5-oxo-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

• 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。