cis-ethyl 4-acetoxy-1-benzyl-3-fluoropyrrolidine-3-carboxylate | 1058142-05-4

• 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: cis-ethyl 4-acetoxy-1-benzyl-3-fluoropyrrolidine-3-carboxylate
• 英文别名: (3S,4R)-ethyl 4-acetoxy-1-benzyl-3-fluoropyrrolidine-3-carboxylate
• CAS: 1058142-05-4
• 化学式: C₁₆H₂₀FNO₄
• 分子量: 309.338
• InChiKey: LWNZKMJYEHGDOC-ZBFHGGJFSA-N

物化性质

• 沸点：
  361.5±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  cis-ethyl 4-acetoxy-1-benzyl-3-fluoropyrrolidine-3-carboxylate 在 甲醇 、 锂硼氢 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  A β-Fluoroamine Inhibitor of Purine Nucleoside Phosphorylase

  摘要：

  The potent immucillin purine nucleoside phosphorylase (PNP) inhibitors F-DADMe-ImmH [(3S,4S)-3], and [(3R,4R)-3] are synthesized in seven steps. Cycloaddition to a fluoroalkene and an enzymic resolution are the key features of the construction of the fluoropyrrolidines 11, from which the immucillins are assembled by use of a three-component Mannich reaction. Slow-onset binding constants (K(i)*) for [(3S,4S)-3] and [(3R,4R)-3] with human PNP are 0.032 and 1.82 nM, respectively. F-DADMe-ImmH [(3S,4S)-3] exhibits oral availability in mice at doses as low as 0.2 mg/kg.

  DOI：

  10.1021/jm800792b
• 作为产物：
  描述：

  Z-ethyl 3-acetoxy-2-fluoroacrylate 、 N-(甲氧甲基)-N-(三甲基硅甲基)苄胺 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以64%的产率得到cis-ethyl 4-acetoxy-1-benzyl-3-fluoropyrrolidine-3-carboxylate
  参考文献：
  名称：

  A β-Fluoroamine Inhibitor of Purine Nucleoside Phosphorylase

  摘要：

  The potent immucillin purine nucleoside phosphorylase (PNP) inhibitors F-DADMe-ImmH [(3S,4S)-3], and [(3R,4R)-3] are synthesized in seven steps. Cycloaddition to a fluoroalkene and an enzymic resolution are the key features of the construction of the fluoropyrrolidines 11, from which the immucillins are assembled by use of a three-component Mannich reaction. Slow-onset binding constants (K(i)*) for [(3S,4S)-3] and [(3R,4R)-3] with human PNP are 0.032 and 1.82 nM, respectively. F-DADMe-ImmH [(3S,4S)-3] exhibits oral availability in mice at doses as low as 0.2 mg/kg.

  DOI：

  10.1021/jm800792b