(2R,5R)-2-tert-butyl-3-methyl-5-phenyl-4-imidazolidinone-trichloroacetic acid | 1276111-20-6

• 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: (2R,5R)-2-tert-butyl-3-methyl-5-phenyl-4-imidazolidinone-trichloroacetic acid
• 英文别名: (2R,5R)-2-tert-butyl-3-methyl-5-phenyl-4-imidazolidinone trichloroacetic acid salt；(2R,5R)-2-tert-butyl-3-methyl-5-phenyl-4-imidazolidinone*TCA；(2R,5R)-2-tert-butyl-3-methyl-5-phenylimidazolidin-4-one;2,2,2-trichloroacetic acid
• CAS: 1276111-20-6
• 化学式: C₂HCl₃O₂*C₁₄H₂₀N₂O
• 分子量: 395.713
• InChiKey: IDDOXOWTEJRPHH-LOCPCMAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 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：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 甲醇 、 水 、 potassium carbonate 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (2R,5R)-2-tert-butyl-3-methyl-5-phenyl-4-imidazolidinone-trichloroacetic acid
  参考文献：
  名称：

  Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis

  摘要：

  The enantioselective alpha-arylation of aldehydes has been accomplished using diaiyliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.

  DOI：

  10.1021/ja2008906
• 作为试剂：
  描述：

  正辛醛 、 二苯基碘三氟甲烷磺酸盐 在 (2R,5R)-2-tert-butyl-3-methyl-5-phenyl-4-imidazolidinone-trichloroacetic acid 、 碳酸氢钠 、 copper(I) bromide 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 3.0h， 以91%的产率得到(S)-2-phenyloctanal
  参考文献：
  名称：

  Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis

  摘要：

  The enantioselective alpha-arylation of aldehydes has been accomplished using diaiyliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.

  DOI：

  10.1021/ja2008906

文献信息

• Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis
  作者：Anna E. Allen、David W. C. MacMillan

  DOI：10.1021/ja2008906

  日期：2011.3.30

  The enantioselective alpha-arylation of aldehydes has been accomplished using diaiyliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.