methyl-5,5-(dimethylenedithio)-12(S)-hydroxy-6(E),8(Z),10(E),14(Z)-eicosatetraenoate | 218162-95-9

• 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-5,5-(dimethylenedithio)-12(S)-hydroxy-6(E),8(Z),10(E),14(Z)-eicosatetraenoate
• 英文别名: methyl 4-[2-[(1E,3Z,5E,7S,9Z)-7-hydroxypentadeca-1,3,5,9-tetraenyl]-1,3-dithiolan-2-yl]butanoate
• CAS: 218162-95-9
• 化学式: C₂₃H₃₆O₃S₂
• 分子量: 424.669
• InChiKey: YZHNWDUDQOSYQS-LWGHFZNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl-5,5-(dimethylenedithio)-12(S)-hydroxy-6(E),8(Z),10(E),14(Z)-eicosatetraenoate 在 lithium hydroxide 、 阻聚剂701 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：

  (2R,3S)-(Z)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-undecene-1,2,3-triol 在 六甲基磷酰三胺 、 四溴化碳 、 双硫磷 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 sodium hydride 、 二异丁基氢化铝 、 过碘酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl-5,5-(dimethylenedithio)-12(S)-hydroxy-6(E),8(Z),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

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.