(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraene-1,6-diyl dimethanesulfonate | 1357293-91-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraene-1,6-diyl dimethanesulfonate
• 英文别名: [(8Z,11Z,14Z,17Z)-5-methylsulfonyloxyicosa-8,11,14,17-tetraenyl] methanesulfonate
• CAS: 1357293-91-4
• 化学式: C₂₂H₃₈O₆S₂
• 分子量: 462.672
• InChiKey: KQJSDCGRLVBIMF-AFSLFLIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraene-1,6-diyl dimethanesulfonate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以84%的产率得到(3Z,6Z,9Z,12Z)-eicosa-3,6,9,12-tetraene
  参考文献：
  名称：

  A practical synthesis of (all-Z)-eicosa-3,6,9,12-tetraene, a pheromone component isolated from emerald moths

  摘要：

  A short and practical synthesis of (all-Z)-eicosa-3,6,9,12-tetraene, a component of the emerald moth pheromone is reported. Two different methodologies are used both starting with the natural polyunsaturated fatty acid (all-Z)-eicosa-5,8,11,14,17-pentaenoic acid (EPA). The methodology can be used for the syntheses of a homologous series of analogues of the pheromone that may be practical for analytical purposes of similar natural products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.039
• 作为产物：
  描述：

  EPA乙酯 在 lithium aluminium tetrahydride 、 lithium hydroxide monohydrate 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraene-1,6-diyl dimethanesulfonate
  参考文献：
  名称：

  A practical synthesis of (all-Z)-eicosa-3,6,9,12-tetraene, a pheromone component isolated from emerald moths

  摘要：

  A short and practical synthesis of (all-Z)-eicosa-3,6,9,12-tetraene, a component of the emerald moth pheromone is reported. Two different methodologies are used both starting with the natural polyunsaturated fatty acid (all-Z)-eicosa-5,8,11,14,17-pentaenoic acid (EPA). The methodology can be used for the syntheses of a homologous series of analogues of the pheromone that may be practical for analytical purposes of similar natural products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.039

文献信息

• A practical synthesis of (all-Z)-eicosa-3,6,9,12-tetraene, a pheromone component isolated from emerald moths
  作者：Anne Marie Langseter、Lars Skattebøl、Yngve Stenstrøm

  DOI：10.1016/j.tetlet.2011.12.039

  日期：2012.2

  A short and practical synthesis of (all-Z)-eicosa-3,6,9,12-tetraene, a component of the emerald moth pheromone is reported. Two different methodologies are used both starting with the natural polyunsaturated fatty acid (all-Z)-eicosa-5,8,11,14,17-pentaenoic acid (EPA). The methodology can be used for the syntheses of a homologous series of analogues of the pheromone that may be practical for analytical purposes of similar natural products. (C) 2011 Elsevier Ltd. All rights reserved.