(E)-3-十八碳烯-13-炔-1-醇乙酸酯 | 71393-99-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (E)-3-十八碳烯-13-炔-1-醇乙酸酯
• 英文名称: (E)-octadec-3-en-13-yn-1-yl acetate
• 英文别名: (E)-3-Octadecen-13-yn-1-ol acetate；[(E)-octadec-3-en-13-ynyl] acetate
• CAS: 71393-99-2
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: QSKLPKHRKLRZFM-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-十八碳烯-13-炔-1-醇乙酸酯 在 Lindlar's catalyst 氢气 作用下， 以 正己烷 为溶剂， 反应 40.0h， 以97%的产率得到(3E,13Z)-十八碳二烯-1-基乙酸酯
  参考文献：
  名称：

  Sequential alkynylation of ω-bromoalkyl triflates: facile access to unsymmetrical non-conjugated diynes including precursors to diene pheromones

  摘要：

  Sequential treatment of omega-bromoalkyl triflates with an alkynyllithium at 0 degreesC followed by addition of a second alkynyllithium and NaI and heating the reaction mixture provides a simple one-pot access to unsymmetrical diynes in good yields. These diynes may be transformed stereoselectively into diene pheromones such as (Z,Z)- and (E,Z)-3,13-octadecadienyl acetate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.094
• 作为产物：
  描述：

  8-溴-1-辛醇 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 25.25h， 生成 (E)-3-十八碳烯-13-炔-1-醇乙酸酯
  参考文献：
  名称：

  Sequential alkynylation of ω-bromoalkyl triflates: facile access to unsymmetrical non-conjugated diynes including precursors to diene pheromones

  摘要：

  Sequential treatment of omega-bromoalkyl triflates with an alkynyllithium at 0 degreesC followed by addition of a second alkynyllithium and NaI and heating the reaction mixture provides a simple one-pot access to unsymmetrical diynes in good yields. These diynes may be transformed stereoselectively into diene pheromones such as (Z,Z)- and (E,Z)-3,13-octadecadienyl acetate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.094

文献信息

• Sequential alkynylation of ω-bromoalkyl triflates: facile access to unsymmetrical non-conjugated diynes including precursors to diene pheromones
  作者：Rosemary J. Armstrong-Chong、Kristopher Matthews、J. Michael Chong

  DOI：10.1016/j.tet.2004.08.094

  日期：2004.11

  Sequential treatment of omega-bromoalkyl triflates with an alkynyllithium at 0 degreesC followed by addition of a second alkynyllithium and NaI and heating the reaction mixture provides a simple one-pot access to unsymmetrical diynes in good yields. These diynes may be transformed stereoselectively into diene pheromones such as (Z,Z)- and (E,Z)-3,13-octadecadienyl acetate. (C) 2004 Elsevier Ltd. All rights reserved.