(3E,6Z,9E)-3,6,9-dodecatrien-1-ol | 171015-41-1

• 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: (3E,6Z,9E)-3,6,9-dodecatrien-1-ol
• CAS: 171015-41-1
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: OFAUAWIRDOCHFP-BXPSWRNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  13.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (3E,6Z,9E)-3,6,9-dodecatrien-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到(3E,6Z,9E)-1-iododeca-3,6,9-triene
  参考文献：
  名称：

  Synthesis of methyl (5Z, 8Z, 11E, 14Z, 17Z)- and (5Z, 8Z, 11E, 14Z, 17E)-eicosapentaenoate (EPA Δ 11t and Δ11t, 17t)

  摘要：

  The ylide of [(E)-6-(tetrahydropyranyloxy)hex-3-enyl] iodide, a common intermediate in the synthesis of EPA Delta 11t and Delta 11t,17t was condensed with (E)- or (Z)-3-hexenal to afford a C12 trienic ether. After transformation of the tetrahydropyranyl ether function into a phosphonium salt in four steps, a second Wittig reaction between the ylide of this salt and a C8 (Z)-unsaturated aldehyde ester provided the title compounds with a purity > 95%.

  DOI：

  10.1016/0009-3084(95)02485-2
• 作为产物：
  描述：

  (E)-己-3-烯醛 在 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (3E,6Z,9E)-3,6,9-dodecatrien-1-ol
  参考文献：
  名称：

  Synthesis of methyl (5Z, 8Z, 11E, 14Z, 17Z)- and (5Z, 8Z, 11E, 14Z, 17E)-eicosapentaenoate (EPA Δ 11t and Δ11t, 17t)

  摘要：

  The ylide of [(E)-6-(tetrahydropyranyloxy)hex-3-enyl] iodide, a common intermediate in the synthesis of EPA Delta 11t and Delta 11t,17t was condensed with (E)- or (Z)-3-hexenal to afford a C12 trienic ether. After transformation of the tetrahydropyranyl ether function into a phosphonium salt in four steps, a second Wittig reaction between the ylide of this salt and a C8 (Z)-unsaturated aldehyde ester provided the title compounds with a purity > 95%.

  DOI：

  10.1016/0009-3084(95)02485-2

文献信息

• Synthesis of methyl (5Z, 8Z, 11E, 14Z, 17Z)- and (5Z, 8Z, 11E, 14Z, 17E)-eicosapentaenoate (EPA Δ 11t and Δ11t, 17t)
  作者：Jean-Michel Vatèle、Huynh Dong Doan、Bernard Fenet、Jean-Michel Chardigny、Jean-Louis Sébédio

  DOI：10.1016/0009-3084(95)02485-2

  日期：1995.10

  The ylide of [(E)-6-(tetrahydropyranyloxy)hex-3-enyl] iodide, a common intermediate in the synthesis of EPA Delta 11t and Delta 11t,17t was condensed with (E)- or (Z)-3-hexenal to afford a C12 trienic ether. After transformation of the tetrahydropyranyl ether function into a phosphonium salt in four steps, a second Wittig reaction between the ylide of this salt and a C8 (Z)-unsaturated aldehyde ester provided the title compounds with a purity > 95%.