ethyl (7Z,13S,14E)-15-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(diphenyl)silyl]oxy]-2-ethylcyclopentyl]-13-hydroxypentadeca-7,14-dien-4,10-diynoate | 1028041-20-4

• 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: ethyl (7Z,13S,14E)-15-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(diphenyl)silyl]oxy]-2-ethylcyclopentyl]-13-hydroxypentadeca-7,14-dien-4,10-diynoate
• CAS: 1028041-20-4
• 化学式: C₅₆H₇₀O₅Si₂
• 分子量: 879.34
• InChiKey: ZELVUNYSTJDNTB-MFNBIMHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.92
• 重原子数：
  63
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (7Z,13S,14E)-15-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(diphenyl)silyl]oxy]-2-ethylcyclopentyl]-13-hydroxypentadeca-7,14-dien-4,10-diynoate 在 P-2 Ni 氢气 、 乙二胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以77%的产率得到
  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
• 作为产物：
  描述：

  (E,3S)-1-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(diphenyl)silyl]oxy]-2-ethylcyclopentyl]hex-1-en-5-yn-3-ol 、 (Z)-4-chloro-but-2-en-1-ol 在 copper(l) iodide 、 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以51%的产率得到ethyl (7Z,13S,14E)-15-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(diphenyl)silyl]oxy]-2-ethylcyclopentyl]-13-hydroxypentadeca-7,14-dien-4,10-diynoate
  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