(11Z,19Z)-(R)-11,19-octacosadiene-1,3-diol 1-p-methoxybenzyl ether | 1246078-15-8

• 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: (11Z,19Z)-(R)-11,19-octacosadiene-1,3-diol 1-p-methoxybenzyl ether
• CAS: 1246078-15-8
• 化学式: C₃₆H₆₂O₃
• 分子量: 542.886
• InChiKey: ITHZFYYZYNMZBS-ZUUHAXCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  39.0
• 可旋转键数：
  28.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (11Z,19Z)-(R)-11,19-octacosadiene-1,3-diol 1-p-methoxybenzyl ether 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 72.0h， 以90%的产率得到(11Z,19Z)-(R)-3-acetoxy-11,19-octacosadien-1-ol p-methoxybenzyl ether
  参考文献：
  名称：

  Pheromone synthesis. Part 244: Synthesis of the racemate and enantiomers of (11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol), a new sex pheromone of male Drosophila melanogaster to show its (S)-isomer and racemate as bioactive

  摘要：

  The enantiomers of (11Z,19Z)-3-acetoxy-11,19-octacosadien-1-ol were synthesized from the enantiomers of 3,4-epoxy-1-butanol PMB ether. Its racemate was also synthesized. Its (S)-isomer and racemate were shown to possess the same pheromone activity as CH503, a long-lived inhibitor of male courtship in Drosophila melanogaster, although the racemate was less active. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.080
• 作为产物：
  描述：

  11,19-octacosadiyne-1,3-diol 1-PMB ether 在 bis(cyclohexanyl)borane 、 溶剂黄146 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以65%的产率得到(11Z,19Z)-(R)-11,19-octacosadiene-1,3-diol 1-p-methoxybenzyl ether
  参考文献：
  名称：

  Pheromone synthesis. Part 244: Synthesis of the racemate and enantiomers of (11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol), a new sex pheromone of male Drosophila melanogaster to show its (S)-isomer and racemate as bioactive

  摘要：

  The enantiomers of (11Z,19Z)-3-acetoxy-11,19-octacosadien-1-ol were synthesized from the enantiomers of 3,4-epoxy-1-butanol PMB ether. Its racemate was also synthesized. Its (S)-isomer and racemate were shown to possess the same pheromone activity as CH503, a long-lived inhibitor of male courtship in Drosophila melanogaster, although the racemate was less active. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.080