methyl (8Z,11Z,14Z)-5-oxoicosa-8,11,14-trienoate | 87141-51-3

• 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 (8Z,11Z,14Z)-5-oxoicosa-8,11,14-trienoate
• CAS: 87141-51-3
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: WAYPMOQITIJRAV-JPFHKJGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (8Z,11Z,14Z)-5-oxoicosa-8,11,14-trienoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到5-oxo-8(Z),11(Z),14(Z)-eicosatrienoic acid
  参考文献：
  名称：

  Total Synthesis of a Potent Proinflammatory 5-Oxo-ETE and Its 6,7-Dihydro Biotransformation Product

  摘要：

  The first total synthesis of a potent inflammatory mediator 5-oxo-6(E),8(Z), 11(Z),14(Z)-eicosatetraenoic acid (5-oxo-ETE) 2 and its biotransformation product 6,7-dihydro-5-oxo-ETE 5 is reported. A convergent synthesis for the unstable title compounds is accomplished via two synthons, dithiolane aldehyde 13 and bisdienyl phosphonium bromide 19. The synthetic 5-oxo-ETE 2 and its 8,9-trans isomer 3 were used to unequivocally confirm the structure of the biologically derived mediators. In addition, using synthetic 6,7-dihydro-5-oxo-ETE 5 we have been able to identify in neutrophils the formation of 6,7-dihydro-5-oxo-ETE 5.

  DOI：

  10.1021/jo9716993
• 作为产物：
  描述：

  Methyl 4-(2-formyl-1,3-dithiolan-2-yl)butanoate 在 bis-(trifluoroacetoxy)-iodo-benzene 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 水 、 乙腈 、 苯 为溶剂， 反应 1.91h， 生成 methyl (8Z,11Z,14Z)-5-oxoicosa-8,11,14-trienoate
  参考文献：
  名称：

  Total Synthesis of a Potent Proinflammatory 5-Oxo-ETE and Its 6,7-Dihydro Biotransformation Product

  摘要：

  The first total synthesis of a potent inflammatory mediator 5-oxo-6(E),8(Z), 11(Z),14(Z)-eicosatetraenoic acid (5-oxo-ETE) 2 and its biotransformation product 6,7-dihydro-5-oxo-ETE 5 is reported. A convergent synthesis for the unstable title compounds is accomplished via two synthons, dithiolane aldehyde 13 and bisdienyl phosphonium bromide 19. The synthetic 5-oxo-ETE 2 and its 8,9-trans isomer 3 were used to unequivocally confirm the structure of the biologically derived mediators. In addition, using synthetic 6,7-dihydro-5-oxo-ETE 5 we have been able to identify in neutrophils the formation of 6,7-dihydro-5-oxo-ETE 5.

  DOI：

  10.1021/jo9716993

文献信息

• Formation and structure determination of 5,6-epoxy-8,11,14-eicosatrienoic acid and 5-oxo-8,11,14-z-eicosatrienoic acid
  作者：Bernd Spur、Attilio Crea、Wilfried Peters、Wolfgang König

  DOI：10.1016/s0040-4039(00)81762-1

  日期：1983.1
• Total Synthesis of a Potent Proinflammatory 5-Oxo-ETE and Its 6,7-Dihydro Biotransformation Product
  作者：Subhash P. Khanapure、Xiao-Xin Shi、William S. Powell、Joshua Rokach

  DOI：10.1021/jo9716993

  日期：1998.1.1

  The first total synthesis of a potent inflammatory mediator 5-oxo-6(E),8(Z), 11(Z),14(Z)-eicosatetraenoic acid (5-oxo-ETE) 2 and its biotransformation product 6,7-dihydro-5-oxo-ETE 5 is reported. A convergent synthesis for the unstable title compounds is accomplished via two synthons, dithiolane aldehyde 13 and bisdienyl phosphonium bromide 19. The synthetic 5-oxo-ETE 2 and its 8,9-trans isomer 3 were used to unequivocally confirm the structure of the biologically derived mediators. In addition, using synthetic 6,7-dihydro-5-oxo-ETE 5 we have been able to identify in neutrophils the formation of 6,7-dihydro-5-oxo-ETE 5.