(3Z,6Z,9Z,12Z)-eicosa-3,6,9,12-tetraene | 1185651-75-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (3Z,6Z,9Z,12Z)-eicosa-3,6,9,12-tetraene
• 英文别名: (3Z,6Z,9Z,12Z)-3,6,9,12-icosatetraene；(3Z,6Z,9Z,12Z)-icosa-3,6,9,12-tetraene；3Z,6Z,9Z,12Z-eicosatetraene
• CAS: 1185651-75-5
• 化学式: C₂₀H₃₄
• 分子量: 274.49
• InChiKey: BGXLLGYBDSOFJB-PPEBMUNXSA-N

物化性质

• 沸点：
  359.8±37.0 °C(Predicted)
• 密度：
  0.823±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 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 16.0h， 生成 (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

文献信息

• (6Z,9Z,12Z)-6,9,12-Octadecatriene and (3Z,6Z,9Z,12Z)-3,6,9,12-icosatetraene, the novel sex pheromones produced by emerald moths
  作者：Rei Yamakawa、Nguyen Duc Do、Yasushi Adachi、Masakatsu Kinjo、Tetsu Ando

  DOI：10.1016/j.tetlet.2009.06.027

  日期：2009.8

  (6Z,9Z,12Z)-6,9,12-Octadecatriene and (3Z,6Z,9Z,12Z)-3,6,9,12-icosatetraene, hydrocarbons unsaturated more highly than usual lepidopteran Type II pheromones, were identified from geometrid females of Hemithea tritonaria and Thalassodes immissaria intaminata, respectively. The triene was synthesized by a double Wittig reaction between hexanal and an ylide derived from (Z)-1,6-diiodo-3-hexene, and the tetraene was synthesized by a coupling between (Z)-3-undecenal and an ylide derived from (3Z,6Z)-1-iodo-3,6-nonadiene. Each synthetic compound attracted males of the corresponding emerald moths in a field. (C) 2009 Elsevier Ltd. All rights reserved.

  根据 (6Z,9Z,12Z)-6,9,12-十八碳三烯和 (3Z,6Z,9Z,12Z)-3,6,9,12-二十碳四烯，这两种烃类化合物比通常的鳞翅目昆虫II型性外激素具有更高的不饱和度，分别从橘斑斜纹夜蛾（Hemithea tritonaria）和黑边绿舟蛾（Thalassodes immissaria intaminata）的雌蛾中鉴定出来。三烯通过己醛与由 (Z)-1,6-二碘-3-己烯衍生的亚胺基进行双 Wittig 反应合成，而四烯则通过 (Z)-3-十一醛与由 (3Z,6Z)-1-碘-3,6-壬二烯衍生的亚胺基进行偶联反应合成。每种合成的化合物都能在田间吸引相应绿舟蛾的雄蛾。(C) 2009 Elsevier Ltd. 保留所有权利。
• A nine carbon homologating system for skip-conjugated polyenes
  作者：Hussein H. Mustafa、Mark S. Baird、Juma’a R. Al Dulayymi、Viacheslav V. Tverezovskiy

  DOI：10.1016/j.chemphyslip.2014.04.005

  日期：2014.10

  Ozonolysis of Z,Z,Z-cylonona-1,4,7-triene leads to a 1,9-difunctionalised Z,Z-3,6-nonadiene which is readily converted into a range of polyunsaturated pheromones and fatty acids. (C) 2014 Elsevier Ireland Ltd. All rights reserved.
• 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.