(2R,5S)-2,3,5-trimethylimidazolidin-4-one | 834862-76-9

• 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: (2R,5S)-2,3,5-trimethylimidazolidin-4-one
• CAS: 834862-76-9
• 化学式: C₆H₁₂N₂O
• 分子量: 128.174
• InChiKey: ZXYYONQPJNODIJ-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  benzyl (2S,5S)-2,3,5-trimethyl-4-oxoimidazolidine-1-carboxylate 在 palladium hydroxide on carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 6.0h， 以41%的产率得到(2R,5S)-2,3,5-trimethylimidazolidin-4-one
  参考文献：
  名称：

  Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

  摘要：

  The first enantioselective, organocatalytic alpha-trifluoromethytation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

  DOI：

  10.1021/ja9053338
• 作为试剂：
  描述：

  三氟碘甲烷 、 adamantan-1-ylacetaldehyde 在 2,6-二甲基吡啶 、 (2R,5S)-2,3,5-trimethylimidazolidin-4-one 、 Ir(ppy)2(dtb-bpy)PF₆ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (S)-2-(1-adamantyl)-3,3,3-trifluoropropan-1-ol
  参考文献：
  名称：

  Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

  摘要：

  The first enantioselective, organocatalytic alpha-trifluoromethytation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

  DOI：

  10.1021/ja9053338

文献信息

• Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis
  作者：David A. Nagib、Mark E. Scott、David W. C. MacMillan

  DOI：10.1021/ja9053338

  日期：2009.8.12

  The first enantioselective, organocatalytic alpha-trifluoromethytation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.