(9E)-9,13-tetradecadien-11-yn-1-ol | 138039-07-3

• 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: (9E)-9,13-tetradecadien-11-yn-1-ol
• 英文别名: (E)-9,13-tetradecadien-11-yn-1-ol；(9E)-tetradeca-9,13-dien-11-yn-1-ol
• CAS: 138039-07-3
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: RHKXBFISNJFBTI-AATRIKPKSA-N

物化性质

• 沸点：
  318.8±15.0 °C(Predicted)
• 密度：
  0.900±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (9E)-9,13-tetradecadien-11-yn-1-ol 在 potassium cyanide 、 锌 作用下， 以 丙醇 、 水 为溶剂， 反应 24.0h， 以91%的产率得到(E,Z)-9,11,13-tetradecatrienol
  参考文献：
  名称：

  Stereospecific synthesis of 1,5-dien-3-ynes and 1,3,5-trienes application to the stereochemical identification of trienic sex pheromones

  摘要：

  A one-pot stereospecific synthesis of 1,5-dien-3-ynes (Z) or (E) is described, based upon a palladium-catalyzed cross-coupling reaction between butenynylzinc bromide, generated in situ from 1,1-difluoroethylene, and an adequate iodoalkene. These dienynes are converted into the corresponding trienic compounds by (Z) semi-hydrogenation.

  DOI：

  10.1016/s0040-4020(01)81934-7
• 作为产物：
  描述：

  1-terbutoxy-9-decyne 在 氢氧化钾 、 四(三苯基膦)钯 、 碘 、 三氯化铁 、 二异丁基氢化铝 、 zinc dibromide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 11.83h， 生成 (9E)-9,13-tetradecadien-11-yn-1-ol
  参考文献：
  名称：

  Stereospecific synthesis of 1,5-dien-3-ynes and 1,3,5-trienes application to the stereochemical identification of trienic sex pheromones

  摘要：

  A one-pot stereospecific synthesis of 1,5-dien-3-ynes (Z) or (E) is described, based upon a palladium-catalyzed cross-coupling reaction between butenynylzinc bromide, generated in situ from 1,1-difluoroethylene, and an adequate iodoalkene. These dienynes are converted into the corresponding trienic compounds by (Z) semi-hydrogenation.

  DOI：

  10.1016/s0040-4020(01)81934-7

文献信息

• (9Z)-9,13-Tetradecadien-11-ynal, the sex pheromone of the avocado seed moth, Stenoma catenifer
  作者：Jocelyn G. Millar、Mark Hoddle、J. Stephen McElfresh、Yunfan Zou、Christina Hoddle

  DOI：10.1016/j.tetlet.2008.06.019

  日期：2008.8

  The highly unsaturated aldehyde (9Z)-9,13-tetradecadien-11-ynal and the corresponding alcohol were identified as possible sex pheromone components of the avocado seed moth, Stenoma catenifer. The aldehyde as a single component attracted more male moths than caged virgin female moths, and addition of the analogous alcohol and/or acetate decreased attraction. A stereospecific synthesis of the pheromone is described. (C) 2008 Elsevier Ltd. All rights reserved.
• Stereospecific synthesis of 1,5-dien-3-ynes and 1,3,5-trienes application to the stereochemical identification of trienic sex pheromones
  作者：Frédérique Tellier、Charles Descoins、Raymond Sauvêtre

  DOI：10.1016/s0040-4020(01)81934-7

  日期：1991.9

  A one-pot stereospecific synthesis of 1,5-dien-3-ynes (Z) or (E) is described, based upon a palladium-catalyzed cross-coupling reaction between butenynylzinc bromide, generated in situ from 1,1-difluoroethylene, and an adequate iodoalkene. These dienynes are converted into the corresponding trienic compounds by (Z) semi-hydrogenation.