rac-(2R,5R)-5-(2-bromophenyl)-1-hydroxy-2-isopropyl-2,3-dimethylimidazolidin-4-one

• 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: rac-(2R,5R)-5-(2-bromophenyl)-1-hydroxy-2-isopropyl-2,3-dimethylimidazolidin-4-one
• 英文别名: (2R,5R)-5-(2-bromophenyl)-1-hydroxy-2,3-dimethyl-2-propan-2-ylimidazolidin-4-one
• 化学式: C₁₄H₁₉BrN₂O₂
• 分子量: 327.221
• InChiKey: MBYURHRAAQQXFK-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻碘溴苯 、 2-isopropyl-1,2-dimethyl-5-oxo-2,5-dihydro-1H-imidazole 3-oxide 在 lithium chloro-isopropyl-magnesium chloride 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 0.25h， 生成 、 rac-(2R,5R)-5-(2-bromophenyl)-1-hydroxy-2-isopropyl-2,3-dimethylimidazolidin-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

文献信息

• Totally diastereoselective addition of aryl Grignard reagents to the nitrone-based chiral glycine equivalent MiPNO
  作者：Maryse Thiverny、Daniel Farran、Christian Philouze、Véronique Blandin、Pierre Y. Chavant

  DOI：10.1016/j.tetasy.2011.07.022

  日期：2011.6

  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.