12-hydroxydodec-3(E)-enoic acid | 73961-79-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 12-hydroxydodec-3(E)-enoic acid
• 英文别名: (E)-12-Hydroxydodec-3-enoic acid
• CAS: 73961-79-2；87372-05-2
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: RRJILZUCEDMMNU-SOFGYWHQSA-N

物化性质

• 沸点：
  379.9±17.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-hydroxydodec-3(E)-enoic acid 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以80%的产率得到(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
• 作为产物：
  描述：

  1-(α-ethoxyethoxy)dec-9-ene 在 sodium chlorite 、 3-甲基-1-环己烯 、 氨基磺酸 、 水 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 臭氧 、 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 7.92h， 生成 12-hydroxydodec-3(E)-enoic acid
  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

• Synthesis of 3(Z)-dodecen-12-olide—an aggregation pheromone of the flat grain beetleCryptolestes pusillus (Coleoptera:Cucujidae)
  作者：A. A. Vasil'ev、L. Engman、V. M. Merkulova

  DOI：10.1007/bf02495778

  日期：2000.7

  Abstract3(Z)-Dodecen-12-olide, an aggregation pheromone of the flat grain beetle, was obtained using 1,4-cis-hydrogenation of ethyl 12-hydroxydodeca-2,4-dienoate as a key step. The dienoic ester was synthesized from 10-hydroxydec-2-enal, which, in turn, was prepared from its saturated precursorvia acetal α-bromination followed by phenylselenation/oxidative elimination/hydrolysis.

  摘要 3(Z)-Dodecen-12-olide 是扁粒甲虫的聚集信息素，以 12-羟基十二-2,4-二烯酸乙酯的 1,4-顺式氢化为关键步骤获得。二烯酸酯是由 10-羟基癸-2-烯醛合成的，而 10-羟基癸-2-烯醛又是由其饱和前体通过缩醛 α-溴化，然后苯硒化/氧化消除/水解制备的。
• 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。
• Process for preparing hydroxycarboxylic acids
  申请人：UNILEVER PLC

  公开号：EP0711746A1

  公开（公告）日：1996-05-15

  A new synthesis of ω-hydroxy acids, which employs commercially available starting materials and lowers the cost of production. The process involves coupling a fatty acyl group by enamine chemistry, followed by a ring expansion and selective reduction of ketoacid.

  一种新的ω-羟基酸合成法，它采用了市场上可买到的起始原料，并降低了生产成本。该工艺包括用烯胺化学方法偶联脂肪酰基，然后进行扩环和选择性还原酮酸。
• Synthesis of allylcarboxylic acids from olefins with diethyl oxomalonate, an enophilic equivalent of carbon dioxide
  作者：Mary F. Salomon、Simon N. Pardo、Robert G. Salomon

  DOI：10.1021/ja00527a064

  日期：1980.3
• 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.