4-[2-[(1E,3Z,6Z,9Z)-pentadeca-1,3,6,9-tetraenyl]-1,3-dithiolan-2-yl]butanoic acid | 201273-29-2

• 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: 4-[2-[(1E,3Z,6Z,9Z)-pentadeca-1,3,6,9-tetraenyl]-1,3-dithiolan-2-yl]butanoic acid
• CAS: 201273-29-2
• 化学式: C₂₂H₃₄O₂S₂
• 分子量: 394.643
• InChiKey: CBFFUUIWNYSAKG-CVJUOOOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[2-[(1E,3Z,6Z,9Z)-pentadeca-1,3,6,9-tetraenyl]-1,3-dithiolan-2-yl]butanoic acid 在 bis-(trifluoroacetoxy)-iodo-benzene 、 阻聚剂701 作用下， 以 甲醇 、 水 为溶剂， 反应 0.03h， 以13%的产率得到5-oxo-6(E),8(E),11(Z),14(Z)-eicosatetraenoic 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 lithium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 水 、 苯 为溶剂， 反应 22.0h， 生成 4-[2-[(1E,3Z,6Z,9Z)-pentadeca-1,3,6,9-tetraenyl]-1,3-dithiolan-2-yl]butanoic 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

文献信息

• 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.
• The Total Synthesis of Tritiated and Deuterated 5-Oxo-ETE, a Novel Inflammatory Mediator
  作者：Subhash P. Khanapure、Xiao-Xin Shi、William S. Powell、Joshua Rokach

  DOI：10.1021/jo980280p

  日期：1998.6.1

  The total synthesis of 11,12,14,15-tetratritiated and deuterated 5-oxo-ETE is accomplished using a novel bisacetylene precursor 14. The syntheses of these labeled derivatives are necessary in order to investigate further the role and biochemistry of the novel inflammatory mediator and eosinophilic chemotactic agent 5-oxo-ETE.