1-(α-ethoxyethoxy)dec-9-ene | 302969-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(α-ethoxyethoxy)dec-9-ene
• 英文别名: 10-(1-Ethoxyethoxy)dec-1-ene
• CAS: 302969-69-3
• 化学式: C₁₄H₂₈O₂
• 分子量: 228.375
• InChiKey: POZQVWBKLARXKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(α-ethoxyethoxy)dec-9-ene 在 Lindlar's catalyst 2,6-二甲基吡啶 、 喹啉 、 sodium periodate 、 重铬酸吡啶 、 正丁基锂 、 氢气 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 间氯过氧苯甲酸 、 二苯二硫醚 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 氘代苯 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.01h， 生成 (11E)-9-hydroxy-13-oxotridec-11-enoic acid
  参考文献：
  名称：

  Total Synthesis of Oxidized Phospholipids. 3. The (11E)-9-Hydroxy-13-oxotridec-11-enoate Ester of 2-Lysophosphatidylcholine

  摘要：

  A total synthesis of (11E)-9-hydroxy-13-oxotridec-11-enoate ester of 2-lysophosphatidylcholine (HOT-PC) was devised to facilitate identification of this oxidized phospholipid. A lactone, 8-(3-oxo-1H,6H-2-oxinyl)octanoic acid (1), believed to be generated through an intermediate (11E)-9-hydroxy-13-oxotridec-11-enoic acid (HOT), is produced upon autoxidation of linoleic acid. A synthesis of lactone 1 methyl ester was accomplished from HOT involving a novel trans-cis isomerization that is driven to completion by cyclization to a hemiacetal. An alternative route to this carbon skeleton was also acheived that provides the lactone 1 itself.

  DOI：

  10.1021/jo000809u
• 作为产物：
  描述：

  9-十烯-1-醇 、 乙烯基乙醚 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以98%的产率得到1-(α-ethoxyethoxy)dec-9-ene
  参考文献：
  名称：

  Concise Synthesis of (3Z)-Dodecen-12-olide, Pheromone Component of the Emerald Ash Borer

  摘要：

  Emerald ash borer (EAB), Agrilus planipennis Fairmaire, is an invasive insect that has killed millions of ash trees in Canada and the USA. (3Z)-Dodecen-12-olide is a known female-produced pheromone of this insect, and a concise, three-step synthesis of a 2:1 blend of (3Z)-dodecen-12-olide and (3E)-dodecen-12-olide starting from commercially available (2-carboxyethyl)triphenylphosphonium bromide and 10-bromo-1-decene is described. The key steps in this synthesis are a lithium-salt-free Wittig reaction and an intramolecular S(N)2 esterification. Both of these macrocyclic lactones are behaviorally active toward EAB, and the 2:1 blend whose synthesis is described here has the potential to be a detection agent, mating disruptor, or mass trapping agent, which could be used in the control of EAB.

  DOI：

  10.1080/00397911.2014.881497

文献信息

• SEX PHEROMONE DERIVATIVES, AND METHODS AND USES THEREOF
  申请人：Her Majesty the Queen in Right of Canada, as rep. by the Minister of Natural Resources Canada

  公开号：US20160205931A1

  公开（公告）日：2016-07-21

  The present disclosure discusses dodecan-12-olide, and formulations thereof, and its use in detection surveys of, and in mitigation methods for, Emerald Ash Borer beetle infestations of Ash trees.

  本公开涉及十二酸酯化十二醇和其制剂，以及其在灰树天牛侵染灰树检测调查和防治方法中的应用。
• Synthesis of (3<i>E</i>)-Dodecen-12-olide, a Potential Pheromone Component of the Emerald Ash Borer
  作者：D. I. MaGee、P. D. Mayo、P. J. Silk、B. Beattie

  DOI：10.1080/00397911.2011.634083

  日期：2013.5.15

  Emerald ash borer (EAB), Agrilus planipennis Fairmaire, is an invasive insect that has killed millions of ash trees in the USA and Canada. A concise synthesis of a potential EAB pheromone component, (3E)-dodecen-12-olide, using highly stereoselective JuliaKocienski olefination as the key step, is reported. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.