2-(2-octenyl)-1,3-dithiane | 158359-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-(2-octenyl)-1,3-dithiane
• 英文别名: 2-[(Z)-oct-2-enyl]-1,3-dithiane
• CAS: 158359-19-4
• 化学式: C₁₂H₂₂S₂
• 分子量: 230.439
• InChiKey: WJNZTAUFCVZZHT-SREVYHEPSA-N

物化性质

• 沸点：
  324.5±25.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-octenyl)-1,3-dithiane 在 盐酸 、 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 methyl (E)-5-[2-[(Z)-oct-2-enyl]-1,3-dithian-2-yl]pent-2-enoate
  参考文献：
  名称：

  Synthesis of 10,11-Dihydro-12-oxo-LTB₄, a Key Biochemical Intermediate

  摘要：

  The first total synthesis of the 5(S)-hydroxy-10,11-dihydro-12-oxo-6(Z),8(E),14(Z)-eicosatrienoic acid (10,11-dihydro-12-oxo-LTB(4)) (3) is reported. This compound is a key pivotal intermediate in the biotransformation of LTB(4) by the so-called ''LTB(4) reductase pathway''.

  DOI：

  10.1021/jo9614957
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 nickel diacetate 氢气 作用下， 以 乙醇 为溶剂， 以94%的产率得到2-(2-octenyl)-1,3-dithiane
  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。
• 12-Oxo-LTB4, a Key Pivotal Intermediate in LTB4 Metabolism
  作者：Subhash P. Khanapure、Sukumar Manna、Joshua Rokach、Robert C. Murphy、Pat Wheelan、William S. Powell

  DOI：10.1021/jo00111a044

  日期：1995.3

  The first total synthesis of the very unstable and elusive biochemical intermediate 5(S)-hydroxy-12-oxo-6(Z),8(E),10(E),14(Z)-eicosatetraenoic acid (12-oxo-LTB(4)) (2) has been accomplished. Incubation of the synthetic 12-oxo-LTB(4) (2) with human keratinocytes produced 5(S),12-dihydroxy-6-glutathionyl-7(E),9(E),14(Z)-eicosatrienoic acid (c-LTB(3)) and 5(S),12-dihydroxy-6-cysteinylglycyl-7(E),9(E),14(Z)-eicosatrienoic acid (d-LTB(3)), two new intriguing mediators which have been identified recently during the incubations of LTB(4) with keratinocytes. We have also confirmed the identity of 12-oxo-LTB(4) prepared from porcine leukocytes by comparison with the synthetic material and identified the formation in these incubates of the 6-trans-isomer of 12-oxo-LTB(4).
• Synthesis of 10,11-Dihydro-12-oxo-LTB₄, a Key Biochemical Intermediate
  作者：Subhash P. Khanapure、Steven S. Wang、William S. Powell、Joshua Rokach

  DOI：10.1021/jo9614957

  日期：1997.1.1

  The first total synthesis of the 5(S)-hydroxy-10,11-dihydro-12-oxo-6(Z),8(E),14(Z)-eicosatrienoic acid (10,11-dihydro-12-oxo-LTB(4)) (3) is reported. This compound is a key pivotal intermediate in the biotransformation of LTB(4) by the so-called ''LTB(4) reductase pathway''.
• 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.