(R)-11-dodecyne-1,3-diol 1-p-methoxybenzyl ether | 1246078-11-4

• 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: (R)-11-dodecyne-1,3-diol 1-p-methoxybenzyl ether
• 英文别名: (3R)-1-[(4-methoxyphenyl)methoxy]dodec-11-yn-3-ol
• CAS: 1246078-11-4
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: QAWGZDINFGPULF-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (R)-11-dodecyne-1,3-diol 1-p-methoxybenzyl ether 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 potassium tert-butylate 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 二乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.25h， 生成 (3R,11E,19Z)-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：

  (2S)-2-[2-(p-methoxybenzyloxy)ethyl]oxirane 在 甲醇 、 potassium carbonate 、 magnesium 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-11-dodecyne-1,3-diol 1-p-methoxybenzyl 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

• 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.
• 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.