(2S,3S)-3-Benzyloxycarbonylamino-2-fluoro-4-phenyl-butyric acid methyl ester | 181047-32-5

• 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: (2S,3S)-3-Benzyloxycarbonylamino-2-fluoro-4-phenyl-butyric acid methyl ester
• CAS: 181047-32-5
• 化学式: C₁₉H₂₀FNO₄
• 分子量: 345.371
• InChiKey: HRKNAHNCEKSNEF-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-Benzyloxycarbonylamino-2-fluoro-4-phenyl-butyric acid methyl ester 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S)-3-Acetylamino-2-fluoro-4-phenyl-butyric acid methyl ester
  参考文献：
  名称：

  Inactivation of serine protease, α-chymotrypsin by fluorinated phenylalanine analogues

  摘要：

  Fluorinated phenylalanine analogues were found to be slow-binding or reversible competitive inhibitors of alpha-chymotrypsin. A series of these compounds were designed to inactivate alpha-chymotrypsin as a result of the formation of hydrogen-bonding between fluorine atom of the inhibitors and the amide protons known as oxy-anion hole in the active-site of serine and cysteine proteases. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00342-3
• 作为产物：
  描述：

  (2R,3S)-3-[(benzyloxycarbonyl)amino]-2-hydroxy-4-phenylbutanoic acid methyl ester 在 二乙胺基三氟化硫 作用下， 以 乙二醇二甲醚 为溶剂， 以55%的产率得到(2S,3S)-3-Benzyloxycarbonylamino-2-fluoro-4-phenyl-butyric acid methyl ester
  参考文献：
  名称：

  Inactivation of serine protease, α-chymotrypsin by fluorinated phenylalanine analogues

  摘要：

  Fluorinated phenylalanine analogues were found to be slow-binding or reversible competitive inhibitors of alpha-chymotrypsin. A series of these compounds were designed to inactivate alpha-chymotrypsin as a result of the formation of hydrogen-bonding between fluorine atom of the inhibitors and the amide protons known as oxy-anion hole in the active-site of serine and cysteine proteases. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00342-3