11,19-octacosadiyne-1,3-diol 1-PMB ether | 1246078-24-9

• 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: 11,19-octacosadiyne-1,3-diol 1-PMB ether
• 英文别名: (S)-11,19-octacosadiyne-1,3-diol 1-p-methoxybenzyl ether；(3S)-1-[(4-methoxyphenyl)methoxy]octacosa-11,19-diyn-3-ol
• CAS: 1246078-24-9
• 化学式: C₃₆H₅₈O₃
• 分子量: 538.855
• InChiKey: GPLYLXZPDSUVRM-DHUJRADRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  39
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 为溶剂， 以79%的产率得到(11Z,19Z)-(S)-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
• 作为产物：
  描述：

  1-Iod-7-hexadecin 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 11,19-octacosadiyne-1,3-diol 1-PMB ether
  参考文献：
  名称：

  Synthesis and Bioassay of the Eight Analogues of the CH503 Male Pheromone (3-Acetoxy-11,19-octacosadien-1-ol) of theDrosophila melanogasterFruit Fly

  摘要：

  合成了 (3R,11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol) 的八种类似物，雄性果蝇的抗催情信息素，用于生物测定。这些是 3-acetoxy-11,19-octacosadiyn-1-ol (1)、3-acetoxyoctacosan-1-ol (2)、(Z)-3-acetoxy-11-octacosen-1-ol (3) 的对映体)和(Z)-3-乙酰氧基-19-八碳烯-1-醇(4)。它们都不具有信息素活性，表明 C-11 和 C-19 处的两个双键对于生物活性是必需的。

  DOI：

  10.1271/bbb.130383

文献信息

• 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
  作者：Kenji Mori、Yasumasa Shikichi、Shruti Shankar、Joanne Y. Yew

  DOI：10.1016/j.tet.2010.06.080

  日期：2010.8

  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.
• Synthesis and Bioassay of the Eight Analogues of the CH503 Male Pheromone (3-Acetoxy-11,19-octacosadien-1-ol) of the<i>Drosophila melanogaster</i>Fruit Fly
  作者：Yasumasa SHIKICHI、Shruti SHANKAR、Joanne Y. YEW、Kenji MORI

  DOI：10.1271/bbb.130383

  日期：2013.9.23

  Eight analogues of (3R,11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol), the anti-aphrodisiac pheromone of male Drosophila melanogaster, were synthesized for a bioassay. These were the enantiomers of 3-acetoxy-11,19-octacosadiyn-1-ol (1), 3-acetoxyoctacosan-1-ol (2), (Z)-3-acetoxy-11-octacosen-1-ol (3), and (Z)-3-acetoxy-19-octacosen-1-ol (4). None of them were pheromonally active, indicating that the two double bonds at C-11 and C-19 were necessary for bioactivity.

  合成了 (3R,11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol) 的八种类似物，雄性果蝇的抗催情信息素，用于生物测定。这些是 3-acetoxy-11,19-octacosadiyn-1-ol (1)、3-acetoxyoctacosan-1-ol (2)、(Z)-3-acetoxy-11-octacosen-1-ol (3) 的对映体)和(Z)-3-乙酰氧基-19-八碳烯-1-醇(4)。它们都不具有信息素活性，表明 C-11 和 C-19 处的两个双键对于生物活性是必需的。