ethyl (3S,4R,1'R,1''S)-<3-(1''-hydroxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate | 228555-90-6

• 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: ethyl (3S,4R,1'R,1''S)-<3-(1''-hydroxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate
• 英文别名: ethyl 2-[(3R,4S)-4-[(1S)-1-hydroxyethyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl]acetate
• CAS: 228555-90-6
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: KOZWTHNCRWNTSG-RPCCPQHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (3S,4R,1'R,1''S)-<3-(1''-hydroxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (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：

  (E,R)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)amine 在 钾硼氢 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 ethyl (3S,4R,1'R,1''S)-<3-(1''-hydroxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate
  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