Methyl 8-(3-hydroxy-5-oxocyclopenten-1-yl)octanoate | 50874-35-6

• 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: Methyl 8-(3-hydroxy-5-oxocyclopenten-1-yl)octanoate
• CAS: 50874-35-6
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: LBJXCCOPAJRKMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 Methyl 8-(3-hydroxy-5-oxocyclopenten-1-yl)octanoate 在 lipase 作用下， 生成 methyl 8-[(3S)-3-hydroxy-5-oxocyclopenten-1-yl]octanoate 、 methyl 8-[(3R)-3-acetyloxy-5-oxocyclopenten-1-yl]octanoate
  参考文献：
  名称：

  First total synthesis of the E type I phytoprostanes

  摘要：

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.042
• 作为产物：
  描述：

  壬二酸氢甲酯 在 sodium tetrahydroborate 、 三乙胺 、 氯乙酰氯 作用下， 以 甲醇 、 四氯化碳 、 水 为溶剂， 生成 Methyl 8-(3-hydroxy-5-oxocyclopenten-1-yl)octanoate
  参考文献：
  名称：

  First total synthesis of the E type I phytoprostanes

  摘要：

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.042

文献信息

• US3970683A
  申请人：——

  公开号：US3970683A

  公开（公告）日：1976-07-20
• US3969391A
  申请人：——

  公开号：US3969391A

  公开（公告）日：1976-07-13
• First total synthesis of the E type I phytoprostanes
  作者：Ana R. Rodrı́guez、Bernd W. Spur

  DOI：10.1016/j.tetlet.2003.08.042

  日期：2003.9

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.