(S,E)-3-tert-butyldimethylsilyloxy-19-octacosen-11-yn-1-ol PMB ether | 1374015-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,E)-3-tert-butyldimethylsilyloxy-19-octacosen-11-yn-1-ol PMB ether
• 英文别名: tert-butyl-[(E,3S)-1-[(4-methoxyphenyl)methoxy]octacos-19-en-11-yn-3-yl]oxy-dimethylsilane
• CAS: 1374015-10-7
• 化学式: C₄₂H₇₄O₃Si
• 分子量: 655.133
• InChiKey: AISTXZXMUWTSEP-JKMQLLHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.37
• 重原子数：
  46
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,E)-3-tert-butyldimethylsilyloxy-19-octacosen-11-yn-1-ol PMB ether 在 吡啶 、 喹啉 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 水 、 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.75h， 生成 (3S,11Z,19E)-3-acetoxy-11,19-octacosadien-1-ol
  参考文献：
  名称：

  Pheromone synthesis. Part 250: Determination of the stereostructure of CH503, a sex pheromone of male Drosophila melanogaster, as (3R,11Z,19Z)-3-acetoxy-11,19-octacosadien-1-ol by synthesis and chromatographic analysis of its eight isomers

  摘要：

  All the eight stereoisomers of 3-acetoxy-11,19-octacosadien-1-ol (1), the male sex pheromone (CH503) of Drosophila melanogaster, were synthesized from two acetylenic starting materials and the enantiomers of 3,4-epoxy-1-butanol PMB ether. Complete separation of the eight isomers of 1 by reversed phase HPLC at -20 degrees C was achieved after their esterification with (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexanecarboxylic acid (27), and the natural CH503 was found to be (3R,11Z19Z)-1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.002
• 作为产物：
  描述：

  7-十六-1-醇 在 吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium iodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (S,E)-3-tert-butyldimethylsilyloxy-19-octacosen-11-yn-1-ol PMB ether
  参考文献：
  名称：

  Pheromone synthesis. Part 250: Determination of the stereostructure of CH503, a sex pheromone of male Drosophila melanogaster, as (3R,11Z,19Z)-3-acetoxy-11,19-octacosadien-1-ol by synthesis and chromatographic analysis of its eight isomers

  摘要：

  All the eight stereoisomers of 3-acetoxy-11,19-octacosadien-1-ol (1), the male sex pheromone (CH503) of Drosophila melanogaster, were synthesized from two acetylenic starting materials and the enantiomers of 3,4-epoxy-1-butanol PMB ether. Complete separation of the eight isomers of 1 by reversed phase HPLC at -20 degrees C was achieved after their esterification with (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexanecarboxylic acid (27), and the natural CH503 was found to be (3R,11Z19Z)-1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.002

文献信息

• 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。
• Pheromone synthesis. Part 250: Determination of the stereostructure of CH503, a sex pheromone of male Drosophila melanogaster, as (3R,11Z,19Z)-3-acetoxy-11,19-octacosadien-1-ol by synthesis and chromatographic analysis of its eight isomers
  作者：Yasumasa Shikichi、Kazuaki Akasaka、Shigeyuki Tamogami、Shruti Shankar、Joanne Y. Yew、Kenji Mori

  DOI：10.1016/j.tet.2012.03.002

  日期：2012.5

  All the eight stereoisomers of 3-acetoxy-11,19-octacosadien-1-ol (1), the male sex pheromone (CH503) of Drosophila melanogaster, were synthesized from two acetylenic starting materials and the enantiomers of 3,4-epoxy-1-butanol PMB ether. Complete separation of the eight isomers of 1 by reversed phase HPLC at -20 degrees C was achieved after their esterification with (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexanecarboxylic acid (27), and the natural CH503 was found to be (3R,11Z19Z)-1. (C) 2012 Elsevier Ltd. All rights reserved.