(Z)-7-((1S,2R)-2-hydroxy-5-oxocyclopent-3-en-1-yl)hept-4-enoic acid | 132803-41-9

• 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: (Z)-7-((1S,2R)-2-hydroxy-5-oxocyclopent-3-en-1-yl)hept-4-enoic acid
• CAS: 132803-41-9
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: BXVIUFIBFZYJCR-MTVLHHSESA-N

物化性质

• 沸点：
  447.1±45.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-((1S,2R)-2-hydroxy-5-oxocyclopent-3-en-1-yl)hept-4-enoic acid 在 咪唑 、 potassium carbonate 、 三氯乙醛 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 16.5h， 生成 (+/-)-methyl 7-<3-<(triethylsilyl)oxy>-5-oxo-1-cyclopenten-1-yl>-4(Z)-heptenoate
  参考文献：
  名称：

  An efficient synthesis of the antisecretory prostaglandin enisoprost

  摘要：

  A 13-step synthesis of the antisecretory prostaglandin enisoprost was previously reported by Collins et al. 1 in 1983. The reported synthesis involved coupling of enone 6 with a cuprate reagent2 derived from a suitably substituted vinylstannane and cuprous pentyne to give enisoprost 10 in 60% yield after removal of protecting groups and chromatographic purification.Further development work on the synthesis of enisoprost has resulted in an improved method for preparing the key enone precursor 6 as outlined in Scheme I. Use of the trans-vinyl iodide 9 in place of the corresponding vinylstannane derivative and use of dilithiocyanocuprate3 coupling technology resulted in an 85% isolated yield of enisoprost 10 as outlined in Scheme II.Direct conversion of the terminal acetylene 8b into protected enisoprost via a one-pot process has also been accomplished as outlined in Scheme II. This latter modification greatly simplified the process and resulted in a 71% isolated yield of enisoprost 10.

  DOI：

  10.1021/jo00007a052
• 作为产物：
  描述：

  methyl 8-(2-furanyl)-8-hydroxy-4(Z)-octenoate 在 水 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 22.0h， 生成 (Z)-7-((1S,2R)-2-hydroxy-5-oxocyclopent-3-en-1-yl)hept-4-enoic acid
  参考文献：
  名称：

  An efficient synthesis of the antisecretory prostaglandin enisoprost

  摘要：

  A 13-step synthesis of the antisecretory prostaglandin enisoprost was previously reported by Collins et al. 1 in 1983. The reported synthesis involved coupling of enone 6 with a cuprate reagent2 derived from a suitably substituted vinylstannane and cuprous pentyne to give enisoprost 10 in 60% yield after removal of protecting groups and chromatographic purification.Further development work on the synthesis of enisoprost has resulted in an improved method for preparing the key enone precursor 6 as outlined in Scheme I. Use of the trans-vinyl iodide 9 in place of the corresponding vinylstannane derivative and use of dilithiocyanocuprate3 coupling technology resulted in an 85% isolated yield of enisoprost 10 as outlined in Scheme II.Direct conversion of the terminal acetylene 8b into protected enisoprost via a one-pot process has also been accomplished as outlined in Scheme II. This latter modification greatly simplified the process and resulted in a 71% isolated yield of enisoprost 10.

  DOI：

  10.1021/jo00007a052