methyl (E)-3-[2-[(Z)-oct-2-enyl]-1,3-dithian-2-yl]prop-2-enoate | 158359-21-8

• 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 (E)-3-[2-[(Z)-oct-2-enyl]-1,3-dithian-2-yl]prop-2-enoate
• CAS: 158359-21-8
• 化学式: C₁₆H₂₆O₂S₂
• 分子量: 314.513
• InChiKey: ZLHOSKPHRSHJBC-QOUMFGDESA-N

物化性质

• 沸点：
  412.1±45.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[2-[(Z)-oct-2-enyl]-1,3-dithian-2-yl]prop-2-enoate 在 lithium hydroxide 、 pyridinium chlorochromate on silica gel 、 二异丁基氢化铝 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 水 为溶剂， 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
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 nickel diacetate 正丁基锂 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 生成 methyl (E)-3-[2-[(Z)-oct-2-enyl]-1,3-dithian-2-yl]prop-2-enoate
  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

• Total synthesis of proinflammatory dihydro-12-KETE metabolites
  作者：Steven S. Wang、Xiao-Xin Shi、William S. Powell、Tamara Tieman、Steven J. Feinmark、Joshua Rokach

  DOI：10.1016/0040-4039(94)02298-p

  日期：1995.1

  The first total synthesis of the 10,11-dihydro-12-etoicosaetranoic acid (10,11-dihydro-12-KETE) , a proinflammatory metabolite of 12-KETE is reported. In addition, the total synthesis of two other potential metabolites of 12-KETE, namely 8,11-dihydro-12-KETE and 8,9-dihydro-12-KETE , is also described. These three synthetic compounds are aimed at investigating a new biosynthetic reductive pathway for

  10,11-二氢-12-的第一全合成ETO二十碳ETRA noic酸（10,11-二氢-12-科特），则报告12-KETE的促炎代谢物。另外，还描述了12-KETE的另外两种潜在的代谢物，即8，11-二氢-12-KETE和8，9-二氢-12-KETE的总合成。这三种合成化合物旨在研究一种新的生物合成还原途径，用于12-羟基二十碳五烯酸（12-HETE）和12-KETE。
• 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.