(3S,11E,19Z)-3-acetoxy-11,19-octacosadien-1-ol | 1374015-20-9

• 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: (3S,11E,19Z)-3-acetoxy-11,19-octacosadien-1-ol
• 英文别名: [(3S,11E,19Z)-1-hydroxyoctacosa-11,19-dien-3-yl] acetate
• CAS: 1374015-20-9
• 化学式: C₃₀H₅₆O₃
• 分子量: 464.773
• InChiKey: GDWNKQCFVVOLED-SNUKZMGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  33
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,11E,19Z)-3-acetoxy-11,19-octacosadien-1-ol 、 (1R,2R)-2-(蒽-2,3-二甲酰亚胺基)环己甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成
  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 、 喹啉 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 potassium tert-butylate 、 水 、 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 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 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， -65.0~140.0 ℃ 、101.33 kPa 条件下， 反应 67.25h， 生成 (3S,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

文献信息

• 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.