(3E)-dodecen-12-olide | 1376306-50-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (3E)-dodecen-12-olide
• 英文别名: (4E)-1-oxacyclotridec-4-en-2-one
• CAS: 1376306-50-1
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: IWDWUDBQBAHLLF-SOFGYWHQSA-N

物化性质

• 沸点：
  335.4±31.0 °C(Predicted)
• 密度：
  0.928±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(α-ethoxyethoxy)dec-9-ene 在 sodium chlorite 、 3-甲基-1-环己烯 、 偶氮二甲酸二异丙酯 、 氨基磺酸 、 水 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 臭氧 、 三苯基膦 、 苏丹红 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙二醇二乙醚 、 水 、 甲苯 为溶剂， 反应 31.92h， 生成 (3E)-dodecen-12-olide
  参考文献：
  名称：

  Synthesis of (3E)-Dodecen-12-olide, a Potential 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 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.

  DOI：

  10.1080/00397911.2011.634083

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。
• COMPOSITION AND METHOD FOR ATTRACTION OF EMERALD ASH BORER AGRILUS PLANIPENNIS FAIRMAIRE (COLEOPTERA: BUPRESTIDAE)
  申请人：SILK Peter J.

  公开号：US20130028858A1

  公开（公告）日：2013-01-31

  The invention disclosed relates to a novel composition and use thereof, for the attraction and detection of emerald ash borer, Agrilus planipennis Fairmaire. The composition comprises (3Z)-dodecen-12-olide and ash foliar or cortical volatiles (green leaf volatiles) associated with a prism trap of a color in the green range of the visible light spectrum. A significant increase in the capture of male A. planipennis is achieved when traps were deployed in the upper tree canopy. This invention is the first demonstration of increased attraction with a combination of a pheromone and a green leaf volatile in a Buprestid species.

  本发明涉及一种新型组合物及其用途，用于吸引和检测翠绿金龟虫（Agrilus planipennis Fairmaire）。该组合物包括（3Z）-十二碳烯酮和与棱柱陷阱相关的灰树叶或皮层挥发物（绿叶挥发物），其颜色在可见光谱的绿色范围内。当陷阱部署在树冠上部时，能够显著增加对雄性A. planipennis的捕获。本发明是首次在Buprestid物种中展示了通过信息素和绿叶挥发物组合增加吸引力的情况。
• Concise Synthesis of (3<i>Z</i>)-Dodecen-12-olide, Pheromone Component of the Emerald Ash Borer
  作者：P. D. Mayo、P. J. Silk、D. I. MaGee、J. McConaghy

  DOI：10.1080/00397911.2014.881497

  日期：2014.7.3

  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.
• Composition and Method for Attraction of Emerald Ash Borer Agrilus Planipennis Fairmaire (Coleoptera: Buprestidae)
  申请人：MAGEE David

  公开号：US20150132252A1

  公开（公告）日：2015-05-14

  The invention disclosed relates to a novel composition and use thereof, for the attraction and detection of emerald ash borer, Agrilus planipennis Fairmaire. The composition comprises (3Z)-dodecen-12-olide and ash foliar or cortical volatiles (green leaf volatiles) associated with a prism trap of a color in the green range of the visible light spectrum. A significant increase in the capture of male A. planipennis is achieved when traps were deployed in the upper tree canopy. This invention is the first demonstration of increased attraction with a combination of a pheromone and a green leaf volatile in a Buprestid species.
• US9226503B2
  申请人：——

  公开号：US9226503B2

  公开（公告）日：2016-01-05