(3R,4S)-3-Acetyl-1-((R)-1-phenyl-ethyl)-4-vinyl-pyrrolidin-2-one | 650599-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4S)-3-Acetyl-1-((R)-1-phenyl-ethyl)-4-vinyl-pyrrolidin-2-one
• 英文别名: (3R,4S)-3-acetyl-4-ethenyl-1-[(1R)-1-phenylethyl]pyrrolidin-2-one
• CAS: 650599-52-3
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: LFNIVLIFNXJOKJ-KYOSRNDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 (3R,4S)-3-Acetyl-1-((R)-1-phenyl-ethyl)-4-vinyl-pyrrolidin-2-one 在 ammonium acetate 、 sodium cyanoborohydride 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以75%的产率得到N-{(S)-1-[(3R,4S)-2-Oxo-1-((R)-1-phenyl-ethyl)-4-vinyl-pyrrolidin-3-yl]-ethyl}-acetamide
  参考文献：
  名称：

  Stereoselective reductive amination of chiral trans-3-acetyl-4-alkylpyrrolidin-2-ones

  摘要：

  trans-3-Acetyl-4-alkyl pyrrolidin-2-ones 5a,b and 8a,b undergo reductive amination with NaBH3(CN) in CH3OH in the presence of CH3COONH4. By acylation of the reaction product the corresponding 3-acylaminoethylpyrrolidin-2-ones 9a-c and 10a,b were obtained with total stereoselection. The configuration of the newly formed stereogenic centre at C-1" of the acylaminoethyl chain was assigned on the basis of H-1 NMR data supported by both molecular mechanics and quantomechanical calculations. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.024

文献信息

• Stereoselective reductive amination of chiral trans-3-acetyl-4-alkylpyrrolidin-2-ones
  作者：Cristiana Fava、Roberta Galeazzi、Giovanna Mobbili、Mario Orena

  DOI：10.1016/j.tetasy.2003.08.024

  日期：2003.11

  trans-3-Acetyl-4-alkyl pyrrolidin-2-ones 5a,b and 8a,b undergo reductive amination with NaBH3(CN) in CH3OH in the presence of CH3COONH4. By acylation of the reaction product the corresponding 3-acylaminoethylpyrrolidin-2-ones 9a-c and 10a,b were obtained with total stereoselection. The configuration of the newly formed stereogenic centre at C-1" of the acylaminoethyl chain was assigned on the basis of H-1 NMR data supported by both molecular mechanics and quantomechanical calculations. (C) 2003 Elsevier Ltd. All rights reserved.