methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate | 218162-94-8

• 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-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate
• CAS: 218162-94-8
• 化学式: C₃₉H₅₄O₃S₂Si
• 分子量: 663.073
• InChiKey: AZXKEUWDZGALDJ-RQASVIAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.65
• 重原子数：
  45.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate 在 lithium hydroxide 、 阻聚剂701 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 生成 5,5-(dimethylenedithio)-12(S)-hydroxy-6(E),8(Z),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：

  Methyl 4-(2-formyl-1,3-dithiolan-2-yl)butanoate 在 六甲基磷酰三胺 、 sodium hexamethyldisilazane 作用下， 以 苯 为溶剂， 反应 18.25h， 生成 methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate
  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