1-Phenyl-2-((S)-2,2,3,5-tetramethyl-4-oxo-imidazolidin-1-yl)-ethane-1,2-dione | 145846-62-4

• 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: 1-Phenyl-2-((S)-2,2,3,5-tetramethyl-4-oxo-imidazolidin-1-yl)-ethane-1,2-dione
• 英文别名: 1-phenyl-2-[(5S)-2,2,3,5-tetramethyl-4-oxoimidazolidin-1-yl]ethane-1,2-dione
• CAS: 145846-62-4
• 化学式: C₁₅H₁₈N₂O₃
• 分子量: 274.32
• InChiKey: DASAPOZGMOCJIK-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Phenyl-2-((S)-2,2,3,5-tetramethyl-4-oxo-imidazolidin-1-yl)-ethane-1,2-dione 在 sodium dithionite 、 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 (S)-1-((R)-2-Hydroxy-2-phenyl-acetyl)-2,2,3,5-tetramethyl-imidazolidin-4-one 、 (S)-1-((S)-2-Hydroxy-2-phenyl-acetyl)-2,2,3,5-tetramethyl-imidazolidin-4-one
  参考文献：
  名称：

  Influence des ultrasons sur la diastéréosélectivité. Synthèse d'imidazolidine-4-one chirales

  摘要：

  A three-step synthesis of imidazolidine-4-one has been realized. Sodium dithionite was a very efficient reagent for the last step, the reduction of a ketone. The reaction is slow under the normal conditions of heating and its diastereoselectivity is poor. Under the influence of ultrasound, the selectivity and the yield are very good. The use of sodium dithionite makes it possible to work in water and to avoid the use of hydrides.

  DOI：

  10.1139/cjc-76-2-234
• 作为产物：
  描述：

  氧代(苯基)乙酰氯 、 (S)-2,2,3,5-tetramethylimidazolidin-4-one 在 三乙胺 作用下， 以 苯 为溶剂， 反应 0.5h， 以70%的产率得到1-Phenyl-2-((S)-2,2,3,5-tetramethyl-4-oxo-imidazolidin-1-yl)-ethane-1,2-dione
  参考文献：
  名称：

  5-Substituted (5S)-imidazolidin-4-ones as effective chiral auxiliary for hydrogenation of ?-keto amides

  摘要：

  The title chiral auxiliary was used for asymmetric catalytic hydrogenation of amides derived from phenylglyoxylic acid to give mandelamides with high diastereoselectivity (diastereoisomeric excess, d. e. up to 96%).

  DOI：

  10.1007/bf00816850

文献信息

• 5-Substituted (5S)-imidazolidin-4-ones as effective chiral auxiliary for hydrogenation of ?-keto amides
  作者：Igor Solodin

  DOI：10.1007/bf00816850

  日期：——

  The title chiral auxiliary was used for asymmetric catalytic hydrogenation of amides derived from phenylglyoxylic acid to give mandelamides with high diastereoselectivity (diastereoisomeric excess, d. e. up to 96%).
• Influence des ultrasons sur la diastéréosélectivité. Synthèse d'imidazolidine-4-one chirales
  作者：Cathy Hubert、Bernard Garrigues

  DOI：10.1139/cjc-76-2-234

  日期：——

  A three-step synthesis of imidazolidine-4-one has been realized. Sodium dithionite was a very efficient reagent for the last step, the reduction of a ketone. The reaction is slow under the normal conditions of heating and its diastereoselectivity is poor. Under the influence of ultrasound, the selectivity and the yield are very good. The use of sodium dithionite makes it possible to work in water and to avoid the use of hydrides.