13-F4t-NeuroP | 1028042-15-0

• 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: 13-F4t-NeuroP
• 英文别名: (4Z,7Z,10Z,13S,14E)-15-[(1S,2R,3R,5S)-2-ethyl-3,5-dihydroxycyclopentyl]-13-hydroxypentadeca-4,7,10,14-tetraenoic acid
• CAS: 1028042-15-0
• 化学式: C₂₂H₃₄O₅
• 分子量: 378.509
• InChiKey: BGXODHLJNXZNNX-UHLVPQFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以100%的产率得到13-F4t-NeuroP
  参考文献：
  名称：

  A Potential Route to Neuroprostanes and Isoprostanes: Preparation of the Four Enantiomerically Pure Diastereomers of 13-F_4t-NeuroP

  摘要：

  We report a potential synthetic route to the isoprostanes and the neuroprostanes that could allow ready access to each of the enantiomerically pure diastereomers of the several regioisomers of these important human metabolites. The key transformation in the synthesis is' a highly diastereoselective thermal intramolecular ene reaction. A critical observation is that the four enantiomerically pure diastereomers of an intermediate acetylenic ester are easily separated from one another. Each of these four has been carried on to a different enantiomerically pure diastereomer of 13-F(4t)-neuroprostane.

  DOI：

  10.1021/jo702600v

文献信息

• A Potential Route to Neuroprostanes and Isoprostanes: Preparation of the Four Enantiomerically Pure Diastereomers of 13-F_4t-NeuroP
  作者：Douglass F. Taber、P. Ganapati Reddy、Kyle O. Arneson

  DOI：10.1021/jo702600v

  日期：2008.5.1

  We report a potential synthetic route to the isoprostanes and the neuroprostanes that could allow ready access to each of the enantiomerically pure diastereomers of the several regioisomers of these important human metabolites. The key transformation in the synthesis is' a highly diastereoselective thermal intramolecular ene reaction. A critical observation is that the four enantiomerically pure diastereomers of an intermediate acetylenic ester are easily separated from one another. Each of these four has been carried on to a different enantiomerically pure diastereomer of 13-F(4t)-neuroprostane.