(4S,5S)-4-Benzyl-5-hydroxymethyl-pyrrolidin-2-one | 745014-67-9

• 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: (4S,5S)-4-Benzyl-5-hydroxymethyl-pyrrolidin-2-one
• CAS: 745014-67-9
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: UZLABTDFMKIAJQ-WDEREUQCSA-N

物化性质

• 沸点：
  429.9±18.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-Benzyl-5-hydroxymethyl-pyrrolidin-2-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 jones reagent 、 硫酸 、 氢气 、 potassium carbonate 、 丙酮 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (2S,3S)-3-Benzyl-pyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Inhibitors of hepatitis C virus NS3·4A protease. Part 3: P2 proline variants

  摘要：

  We recently described the identification of an optimized alpha-ketoamide warhead for our series of HCV NS3(.)4A inhibitors. We report herein a series of HCV protease inhibitors incorporating 3-alkyl-substituted prolines in P-2. These compounds show exceptional enzymatic and cellular potency given their relatively small size. The marked enhancement of activity of these 3-substituted proline derivatives relative to previously reported 4-hydroxyproline derivatives constitutes additional evidence for the importance of the S-2 binding pocket as the defining pharmacophore for inhibition of the NS3(.)4A enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.078
• 作为产物：
  描述：

  α-lithiobenzyl phenyl sulfide 在 盐酸 、 正丁基锂 、 四甲基乙二胺 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 生成 (4S,5S)-4-Benzyl-5-hydroxymethyl-pyrrolidin-2-one
  参考文献：
  名称：

  Inhibitors of hepatitis C virus NS3·4A protease. Part 3: P2 proline variants

  摘要：

  We recently described the identification of an optimized alpha-ketoamide warhead for our series of HCV NS3(.)4A inhibitors. We report herein a series of HCV protease inhibitors incorporating 3-alkyl-substituted prolines in P-2. These compounds show exceptional enzymatic and cellular potency given their relatively small size. The marked enhancement of activity of these 3-substituted proline derivatives relative to previously reported 4-hydroxyproline derivatives constitutes additional evidence for the importance of the S-2 binding pocket as the defining pharmacophore for inhibition of the NS3(.)4A enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.078