(S)-4-Hydroxy-6-phenyl-hex-5-ynoic acid tert-butyl ester | 180858-10-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-4-Hydroxy-6-phenyl-hex-5-ynoic acid tert-butyl ester
• CAS: 180858-10-0
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: OGEPOYKDKVKTLU-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-4-Hydroxy-6-phenyl-hex-5-ynoic acid tert-butyl ester 在 Lindlar catalyst 氢气 作用下， 以 喹啉 、 甲苯 为溶剂， 反应 1.0h， 生成 、
  参考文献：
  名称：

  Stereoselective synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone

  摘要：

  A short (7 steps) and efficient (45% overall yield) synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-gamma-lactone, a versatile intermediate toward possible HIV-1 protease inhibitors, is described. Two examples of trans-alpha-benzylation of the lactonic ring followed by a regioselective opening of the epoxide (with thiopropanamide) as well as an opening of the lactone ring with L-valine (2-methoxy-ethyl)-amide are also given. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00215-7
• 作为产物：
  描述：

  tert-butyl 4-(methoxy(methyl)amino)-4-oxobutanoate 在 sodium hydroxide 、 (S)-alpine borane 、 乙基溴化镁 、 双氧水 作用下， 反应 14.83h， 生成 (S)-4-Hydroxy-6-phenyl-hex-5-ynoic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone

  摘要：

  A short (7 steps) and efficient (45% overall yield) synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-gamma-lactone, a versatile intermediate toward possible HIV-1 protease inhibitors, is described. Two examples of trans-alpha-benzylation of the lactonic ring followed by a regioselective opening of the epoxide (with thiopropanamide) as well as an opening of the lactone ring with L-valine (2-methoxy-ethyl)-amide are also given. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00215-7