ethyl (3S,4R,1'R,1''S)-<3-(1''-methanesulphonyloxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate | 228556-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ethyl (3S,4R,1'R,1''S)-<3-(1''-methanesulphonyloxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate
• CAS: 228556-01-2
• 化学式: C₁₉H₂₇NO₆S
• 分子量: 397.492
• InChiKey: VLPGFHMIYGKDQD-YQYZPQCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  89.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl (3S,4R,1'R,1''S)-<3-(1''-methanesulphonyloxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以79%的产率得到(3R,4R,1'R)-3-ethyl-4-(2''-hydroxyethyl)-1-(1'-phenylethyl)pyrrolidin-2-one
  参考文献：
  名称：

  Stereoselective reduction of chiral trans-3-acetyl-4-alkylpyrrolidin-2-ones

  摘要：

  A number of trans-3-acetyl-4-alkylpyrrolidin-2-ones 8a-d and 11a,b were prepared and reduction of the keto group, carried out with KBH4 in CH3OH, led mainly to 3-hydroxyethylpyrrolidin-2-ones 13a-d and 19a,b with high stereoselection, Configuration of the newly formed stereogenic centre on the hydroxyethyl chain was assigned by H-1 NMR data supported by molecular mechanic calculations and eventually confirmed by X-ray diffraction analysis of p-iodobenzoate derivative 15. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00031-2
• 作为产物：
  描述：

  ethyl (3S,4R,1'R)-<3-acetyl-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate 在 4-二甲氨基吡啶 、 钾硼氢 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 ethyl (3S,4R,1'R,1''S)-<3-(1''-methanesulphonyloxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Stereoselective reduction of chiral trans-3-acetyl-4-alkylpyrrolidin-2-ones

  摘要：

  A number of trans-3-acetyl-4-alkylpyrrolidin-2-ones 8a-d and 11a,b were prepared and reduction of the keto group, carried out with KBH4 in CH3OH, led mainly to 3-hydroxyethylpyrrolidin-2-ones 13a-d and 19a,b with high stereoselection, Configuration of the newly formed stereogenic centre on the hydroxyethyl chain was assigned by H-1 NMR data supported by molecular mechanic calculations and eventually confirmed by X-ray diffraction analysis of p-iodobenzoate derivative 15. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00031-2

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.