(4R,5S)-4-sec-Butyl-5-hydroxymethyl-pyrrolidin-2-one | 745014-40-8

• 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)-4-sec-Butyl-5-hydroxymethyl-pyrrolidin-2-one
• 英文别名: (4R,5S)-4-butan-2-yl-5-(hydroxymethyl)pyrrolidin-2-one
• CAS: 745014-40-8
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: IKBXQZCYGYCQJD-SPDVFEMOSA-N

物化性质

• 沸点：
  342.2±15.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (4R,5S)-4-sec-Butyl-5-hydroxymethyl-pyrrolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 ((2S,3R)-3-sec-Butyl-pyrrolidin-2-yl)-methanol
  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：

  tert-butyl (2S,3R)-3-(but-1-en-2-yl)-2-(((tert-butyldimethylsilyl)-oxy)methyl)-5-oxopyrrolidine-1-carboxylate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， -20.0 ℃ 、101.33 kPa 条件下， 生成 (4R,5S)-4-sec-Butyl-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