(4R,5S)-1,5-dimethyl-4-phenyl-3-[(2R)-2-pyrrolidin-1-ylpropanoyl]imidazolidin-2-one | 206358-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4R,5S)-1,5-dimethyl-4-phenyl-3-[(2R)-2-pyrrolidin-1-ylpropanoyl]imidazolidin-2-one
• CAS: 206358-49-8
• 化学式: C₁₈H₂₅N₃O₂
• 分子量: 315.415
• InChiKey: PMBGXRAUPMZBLU-LZWOXQAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-1,5-dimethyl-4-phenyl-3-[(2R)-2-pyrrolidin-1-ylpropanoyl]imidazolidin-2-one 在 2,6-二甲基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 (4R,5S,2'R)-3-(α-bromopropionyl)-1,5-dimethyl-4-phenylimidazolidin-2-one
  参考文献：
  名称：

  Synthesis of α-amino esters by dynamic kinetic resolution of α-haloacyl imidazolidinones

  摘要：

  Dynamic kinetic resolution of alpha -haloacyl imidazolidinones with a variety of nitrogen and carbon nucleophiles has been achieved with selectivities up to 100% (d.e.). An unusual dichotomy of diastereoselection has been observed whereby metalated nucleophiles preferentially react via the 5S,2 'R diastereomer whilst amine nucleophiles react via the 5S,2 'S diastereomer. Mild procedures are described for the coupling and removal of the ephedrine based chiral auxiliary. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00550-6
• 作为产物：
  描述：

  四氢吡咯 、 (2'RS,4S,5R)-1-N-(2'bromopropanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one 在 四丁基碘化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 46.0h， 生成 (4R,5S)-1,5-dimethyl-4-phenyl-3-[(2S)-2-pyrrolidin-1-ylpropanoyl]imidazolidin-2-one 、 (4R,5S)-1,5-dimethyl-4-phenyl-3-[(2R)-2-pyrrolidin-1-ylpropanoyl]imidazolidin-2-one
  参考文献：
  名称：

  Synthesis of α-amino esters by dynamic kinetic resolution of α-haloacyl imidazolidinones

  摘要：

  Dynamic kinetic resolution of alpha -haloacyl imidazolidinones with a variety of nitrogen and carbon nucleophiles has been achieved with selectivities up to 100% (d.e.). An unusual dichotomy of diastereoselection has been observed whereby metalated nucleophiles preferentially react via the 5S,2 'R diastereomer whilst amine nucleophiles react via the 5S,2 'S diastereomer. Mild procedures are described for the coupling and removal of the ephedrine based chiral auxiliary. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00550-6

文献信息

• Rationalising diastereoselection in the dynamic kinetic resolution of α-haloacyl imidazolidinones
  作者：Stephen Caddick、Kerry Jenkins、Nigel Treweeke、Sara X. Candeias、Carlos A.M. Afonso

  DOI：10.1016/s0040-4039(98)00175-0

  日期：1998.4

  A crossover from S(N)2 to general base catalysed nucleophilic substitution can account for the dichotomous diastereoselectivity observed in DKR reactions of alpha-haloacyl imidazolidinones. Aprotic nucleophiles (Nu(-)) react preferentially with the 5S*,2'R* diastereomer via an S(N)2 mechanism. Conversely, amines (R2NH) generally react preferentially with the 5S*,2'S* diastereomer. General base catalysis via a bifurcated hydrogen bonded assembly accounts for this anomalous stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.