(S)-2,2,3-trimethyl-5-phenylimidazolidin-4-one | 209161-43-3

• 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: (S)-2,2,3-trimethyl-5-phenylimidazolidin-4-one
• 英文别名: (5S)-2,2,3-trimethyl-5-phenylimidazolidin-4-one
• CAS: 209161-43-3
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: GBBKSKGUQMLIHN-JTQLQIEISA-N

物化性质

• 沸点：
  344.7±42.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2,2,3-trimethyl-5-phenylimidazolidin-4-one 在 sodium dithionite 、 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 16.0h， 生成 (5S)-1-[(2R)-2-hydroxy-2-phenylacetyl]-2,2,3-trimethyl-5-phenylimidazolidin-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：

  (S)-2-amino-N-methyl-2-phenylacetamide 、 丙酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到(S)-2,2,3-trimethyl-5-phenylimidazolidin-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

文献信息

• The asymmetric reduction of imidazolinones with trichlorosilane
  作者：Christian Wagner、Andreas F. Kotthaus、Stefan F. Kirsch

  DOI：10.1039/c7cc01561e

  日期：——

  It is shown how imidazolinones are reduced by trichlorosilane in a highly enantioselective fashion when treated with a novel Lewis base organocatalyst that is based on a 2,2'-bispyrrolidine core. Under mild reaction conditions and with low catalyst loading the hydrosilylation reaction provides a broad range of chiral imidazolidinones with various structural motifs including sterically demanding substituents

  显示了当用基于2,2'-双吡咯烷核的新型路易斯碱有机催化剂处理时，三氯硅烷如何以高度对映选择性的方式还原咪唑啉酮类化合物。在温和的反应条件下和较低的催化剂载量下，氢化硅烷化反应提供了具有各种结构基序的手性咪唑啉酮，所述结构基序包括空间上需要的取代基，烷基和芳基。
• 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.