methyl-5,5-(dimethylenedithio)-6(E)-8-oxo-7-octenoate | 201273-27-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: methyl-5,5-(dimethylenedithio)-6(E)-8-oxo-7-octenoate
• 英文别名: methyl 4-[2-[(E)-3-oxoprop-1-enyl]-1,3-dithiolan-2-yl]butanoate
• CAS: 201273-27-0
• 化学式: C₁₁H₁₆O₃S₂
• 分子量: 260.378
• InChiKey: ZGURMBXQYUAGSO-ZZXKWVIFSA-N

物化性质

• 沸点：
  383.2±37.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  94
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl-5,5-(dimethylenedithio)-6(E)-8-oxo-7-octenoate 在 bis-(trifluoroacetoxy)-iodo-benzene 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 以79%的产率得到methyl (6E)-5,8-dioxo-6-octenoate
  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：

  甲酰甲撑基三苯基磷 、 Methyl 4-(2-formyl-1,3-dithiolan-2-yl)butanoate 以 苯 为溶剂， 反应 18.0h， 以56%的产率得到methyl-5,5-(dimethylenedithio)-6(E)-8-oxo-7-octenoate
  参考文献：
  名称：

  The Total Synthesis of 5-Oxo-12(S)-hydroxy-6(E),8(Z),10(E),14(Z)-eicosatetraenoic Acid and Its 8,9-trans-Isomer and Their Identification in Human Platelets

  摘要：

  The first total synthesis of 5-oxo-12(S)-hydroxy-6(E),8(Z),10(E), 14(Z)-eicosatetraenoic acid (5-oxo-12-HETE) 6 and its 8-trans-isomer 7 is reported. The synthetic 5-oxo-12-HETE 6 and its 8,9-trans-isomer 7 were used to identify their formation in mixtures of platelets and neutrophils by transcellular metabolism.

  DOI：

  10.1021/jo9813282

文献信息

• The Total Synthesis of 5-Oxo-12(<i>S</i>)-hydroxy-6(<i>E</i>),8(<i>Z</i>),10(<i>E</i>),14(<i>Z</i>)-eicosatetraenoic Acid and Its 8,9-<i>trans</i>-Isomer and Their Identification in Human Platelets
  作者：Subhash P. Khanapure、William S. Powell、Joshua Rokach

  DOI：10.1021/jo9813282

  日期：1998.11.1

  The first total synthesis of 5-oxo-12(S)-hydroxy-6(E),8(Z),10(E), 14(Z)-eicosatetraenoic acid (5-oxo-12-HETE) 6 and its 8-trans-isomer 7 is reported. The synthetic 5-oxo-12-HETE 6 and its 8,9-trans-isomer 7 were used to identify their formation in mixtures of platelets and neutrophils by transcellular metabolism.
• 5-Oxo-15-HETE: Total synthesis and bioactivity
  作者：Pranav Patel、Jaganmohan R. Anumolu、William S. Powell、Joshua Rokach

  DOI：10.1016/j.bmcl.2011.01.032

  日期：2011.3

  The first total synthesis of 6(E),8(Z),11(Z),13(E) 5-oxo-15-HETE 4 was accomplished. The synthetic material was evaluated with calcium mobilization assay and compared with 5-oxo-ETE the natural ligand for the OXE receptor. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.
• 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.