Methyl 4-(2-formyl-1,3-dithiolan-2-yl)butanoate | 201273-26-9

• 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 4-(2-formyl-1,3-dithiolan-2-yl)butanoate
• CAS: 201273-26-9
• 化学式: C₉H₁₄O₃S₂
• 分子量: 234.34
• InChiKey: FUACRVZLWSXESI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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 4-(2-formyl-1,3-dithiolan-2-yl)butanoate 在 六甲基磷酰三胺 、 lithium hydroxide 、 阻聚剂701 、 四丁基氟化铵 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 36.25h， 生成 5,5-(dimethylenedithio)-12(S)-hydroxy-6(E),8(E),10(E),14(Z)-eicosatetraenoic acid
  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
• 作为产物：
  描述：

  1,3-dithiolane-2-carboxaldehyde 、 4-溴丁酸甲酯 在 sodium hydride 作用下， 以 二甲基亚砜 、 苯 为溶剂， 以55%的产率得到Methyl 4-(2-formyl-1,3-dithiolan-2-yl)butanoate
  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

• 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.
• 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.