(2S,3R)-2-((Z)-oct-2-enyl)-3-nonyloxirane | 135731-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S,3R)-2-((Z)-oct-2-enyl)-3-nonyloxirane
• 英文别名: (6Z)-cis-9S,10R-epoxy-nonadecene；9S,10R-Epoxy-6Z-nonadecene；(2R,3S)-2-nonyl-3-[(Z)-oct-2-enyl]oxirane
• CAS: 135731-94-1
• 化学式: C₁₉H₃₆O
• 分子量: 280.494
• InChiKey: KZUXZKOKPZTLGK-LAJWLBFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2S,3S)-1-tosyloxy-2,3-dodecanediol 在 喹啉 、 正丁基锂 、 氢气 、 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， -78.0~20.0 ℃ 、344.75 kPa 条件下， 反应 7.75h， 生成 (2S,3R)-2-((Z)-oct-2-enyl)-3-nonyloxirane
  参考文献：
  名称：

  Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)

  摘要：

  The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hubner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hubner). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.015

文献信息

• 10.3390/molecules29092136
  作者：Zhou, Yun、Wang, Jianan、Tian, Beijing、Zhu, Yanwei、Zhang, Yujuan、Han, Jinlong、Zhong, Jiangchun、Shan, Chenggang

  DOI：10.3390/molecules29092136

  日期：——

  A concise synthesis of the sex pheromones of elm spanworm as well as painted apple moth has been achieved. The key steps were the alkylation of acetylide ion, Sharpless asymmetric epoxidation and Brown’s P2-Ni reduction. This approach provided the sex pheromone of the elm spanworm (1) in 31% total yield and those of the painted apple moth (2, 3) in 26% and 32% total yields. The ee values of three final

  实现了榆树蛾和苹果蛾性信息素的简明合成。关键步骤是乙炔离子的烷基化、Sharpless不对称环氧化和Brown's P2-Ni还原。该方法提供的榆树蛾 (1) 的性信息素总产量为 31%，苹果蛾 (2, 3) 的性信息素总产量为 26% 和 32%。三种最终产品的ee值均达到99%。合成的信息素在管理和控制这些害虫方面具有广阔的应用前景。
• Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)
  作者：David I. MaGee、Peter J. Silk、Junping Wu、Peter D. Mayo、Krista Ryall

  DOI：10.1016/j.tet.2011.05.015

  日期：2011.7

  The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hubner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hubner). (C) 2011 Elsevier Ltd. All rights reserved.