(5Z,8Z,10E)-11-[2-[(Z)-oct-2-enyl]-1,3-dithian-2-yl]undeca-5,8,10-trienoic acid | 158359-25-2

• 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: (5Z,8Z,10E)-11-[2-[(Z)-oct-2-enyl]-1,3-dithian-2-yl]undeca-5,8,10-trienoic acid
• CAS: 158359-25-2
• 化学式: C₂₃H₃₆O₂S₂
• 分子量: 408.67
• InChiKey: LLINXPGSEDDSFG-BLRGCAAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  (5Z,8Z,10E)-11-[2-[(Z)-oct-2-enyl]-1,3-dithian-2-yl]undeca-5,8,10-trienoic acid 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 生成 (5Z,8E,10E,14Z)-12-oxoicosa-5,8,10,14-tetraenoic acid
  参考文献：
  名称：

  Synthesis of 12-KETE and its 8,9-trans-isomer

  摘要：

  The first total synthesis of the highly unstable biological mediator 12-ketoeicosatetraenoic acid (12-KETE) 3 and its 8,9-trans-isomer 20 is presented. The strategy focuses on the stable precursor dithiane 13 and its conversion to 9 and 20. Biochemical experiments show that the two isomers are not interconverted in vivo, raising the possibility that the trans-isomer 20 may be formed by a primary biochemical mechanism.

  DOI：

  10.1016/s0040-4039(00)73109-1
• 作为产物：
  描述：

  5-氧代戊酸甲酯 在 lithium hydroxide 、 四溴化碳 、 双硫磷 、 四丁基氟化铵 、 sodium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 0.67h， 生成 (5Z,8Z,10E)-11-[2-[(Z)-oct-2-enyl]-1,3-dithian-2-yl]undeca-5,8,10-trienoic acid
  参考文献：
  名称：

  Synthesis of 12-KETE and its 8,9-trans-isomer

  摘要：

  The first total synthesis of the highly unstable biological mediator 12-ketoeicosatetraenoic acid (12-KETE) 3 and its 8,9-trans-isomer 20 is presented. The strategy focuses on the stable precursor dithiane 13 and its conversion to 9 and 20. Biochemical experiments show that the two isomers are not interconverted in vivo, raising the possibility that the trans-isomer 20 may be formed by a primary biochemical mechanism.

  DOI：

  10.1016/s0040-4039(00)73109-1

文献信息

• Synthesis of 12-KETE and its 8,9-trans-isomer
  作者：Steven S. Wang、Joshua Rokach、William S. Powell、Catherine Dekle、Steven J. Feinmark

  DOI：10.1016/s0040-4039(00)73109-1

  日期：1994.6

  The first total synthesis of the highly unstable biological mediator 12-ketoeicosatetraenoic acid (12-KETE) 3 and its 8,9-trans-isomer 20 is presented. The strategy focuses on the stable precursor dithiane 13 and its conversion to 9 and 20. Biochemical experiments show that the two isomers are not interconverted in vivo, raising the possibility that the trans-isomer 20 may be formed by a primary biochemical mechanism.