(Z,E)-9,11,13-tetradecatrienol | 129196-61-8

• 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: (Z,E)-9,11,13-tetradecatrienol
• 英文别名: (z,e)-9,11,13-Tetradecatrien-1-ol；(9Z,11E)-tetradeca-9,11,13-trien-1-ol
• CAS: 129196-61-8
• 化学式: C₁₄H₂₄O
• 分子量: 208.344
• InChiKey: ISALVHMRHHEIHZ-ICWBMWKASA-N

物化性质

• 沸点：
  325.0±11.0 °C(Predicted)
• 密度：
  0.870±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z,E)-9,11,13-tetradecatrienol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以83%的产率得到(Z,E)-9,11,13-tetradecatrienal
  参考文献：
  名称：

  (Z,E)-9,11,13-十四碳三烯醛的合成改进，角豆蛾 Apomyelois (= Ectomyelois) ceratoniae（鳞翅目：Pyralidae）的性信息素

  摘要：

  (Z,E)-9,11,13-Tetradecatrienal 是一种性信息素成分，由角豆蛾 Apomyelois ceratoniae Zeller（鳞翅目：Pyralidae）的处女雌性发出，是伊朗石榴果实的重要害虫。这种害虫的化学控制是不可能的，需要使用信息素的生物方法。与以前相比，性信息素主要成分的合成步骤更少，成本更低。(Z,E)-9,11,13-十四碳三烯醛通过四步合成，总产率为 59%。来自 E-1,2-二氯乙烯的共轭二烯醇中间体与乙烯基溴化镁的偶联以良好的产率实现，然后用活化的锌在 THF-H2O 中还原二烯醇并氧化得到性信息素的醛。

  DOI：

  10.3184/174751917x14894997017450
• 作为产物：
  描述：

  1-terbutoxy-9-decyne 在 potassium cyanide 、 氢氧化钾 、 正丁基锂 、 水 、 三氯化铁 、 zinc dibromide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 丙醇 、 乙醚 、 正己烷 为溶剂， 反应 82.5h， 生成 (Z,E)-9,11,13-tetradecatrienol
  参考文献：
  名称：

  Sex pheromone ofStenoma cecropia Meyrick (Lepidoptera: Elachistidae)

  摘要：

  (Z,E)-9,11-tetradecadienal (Z9,E11-14: Ald; 11%), (Z,E)-9,11,13-tetradecatrienal (Z9,E11, 13-14:Ald; 67%), (Z,E)-9,11-tetradecadienyl acetate (Z9,E11-14:Ac, 5.5%), and (Z,E)-9,11, 13-tetradecatrienyl acetate (Z9,E11,13-14:Ac; 16.5%) were identified in the extracts of female pheromone glands of Stenoma cecropia (Lepidoptera: Elachistidae). From electroantennograms and single sensillum recordings, receptors to Z9,E 11,13-14:Ald and Z9,E11-14:Ald were found on male antenna. Behavioral data were obtained from olfactometric tests in the laboratory and field trapping experiments in Colombia. It appeared that a blend of Z9,E11,13-14:Ald (83%) and Z9,E11-14:Ald (17%) was attractive to males. These aldehydes are assumed to be components of the sex pheromone of S. cecropia, whereas the acetates found in gland extracts might be precursors of the pheromone.

  DOI：

  10.1007/bf02027948

文献信息

• Isolation, identification and synthesis of sex pheromone components of the carob moth, ectomyelois ceratoniae
  作者：T.C. Baker、W. Francke、C. Löfstedt、B.S. Hansson、J.-W. Du、P.L. Phelan、R.S. Vetter、R. Youngman

  DOI：10.1016/s0040-4039(00)99153-6

  日期：1989.1

  The sex pheromone of females of the carob moth, Ectomyelois ceratoniae, was identified to be a mixture of (Z,E)-9,11,13-tetradecatrienal, (Z,E)-9,11-tetradecadienal and (Z)-9-tetradecenal in the ratio of 10:1:1. A synthetic blend proved to be attractive.

  角豆蛾雌性雌性性激素，是（Z，E）-9,11,13-十四碳烯，（Z，E）-9,11-十四碳烯和（Z）-的混合物。9-十四烯的比例为10：1：1。合成的混合物被证明是有吸引力的。
• SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION
  申请人：Provivi, Inc.

  公开号：US20160108436A1

  公开（公告）日：2016-04-21

  In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.

  在某些方面，本发明提供了一种通过将不饱和或饱和的碳氢基质与一种羟化酶酶接触来生产端羟基化烯烃和炔烃的方法。用于执行本发明方法的示例端羟化酶对碳氢基质中的一个端碳具有强选择性，包括但不限于非血红素二铁烷烃单加氧酶、细胞色素P450（例如CYP52和CYP153家族的细胞色素P450）以及长链烷烃羟化酶。在某些实施例中，端羟基化的烯烃或炔烃进一步转化为端烯醛。在某些实施例中，端羟基化的烯烃和炔烃可用作改变昆虫行为的昆虫信息素。在其他实施例中，端羟基化的烯烃和炔烃是通过醋酸化或氧化醇基团来产生信息素的有用中间体。
• Synthesis of olefinic alcohols via enzymatic terminal hydroxylation
  申请人：PROVIVI, INC.

  公开号：US10202620B2

  公开（公告）日：2019-02-12

  In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.

  在某些方面，本发明提供了通过使不饱和或饱和烃底物与羟化酶接触来生产末端羟化的烯烃和炔烃的方法。用于实施本发明方法的典型末端羟化酶对烃底物的一个末端碳具有强选择性，包括但不限于非血红素二铁烷烃单氧化酶、细胞色素 P450（例如 CYP52 和 CYP153 家族的细胞色素 P450）以及长链烷烃羟化酶。在某些实施方案中，末端羟化的烯或炔进一步转化为末端烯醛。在某些实施方案中，末端羟基化的烯烃和炔烃可用作昆虫信息素，改变昆虫的行为。在其他实施方案中，末端羟基化的烯烃和炔烃是通过乙酰化或氧化醇分子生产信息素的有用中间体。
• Stereospecific synthesis of (Z,E)-9,11,13-tetradecatrien-1-yl acetate and aldehyde sex pheromone components of stenoma cecropia and ectomyelois ceratoniae
  作者：Frédérique Tellier、Charles Descoins

  DOI：10.1016/0040-4039(90)80210-d

  日期：1990.1
• Millar, Jocelyn G., Agricultural and Biological Chemistry, 1990, vol. 54, # 9, p. 2473 - 2476
  作者：Millar, Jocelyn G.

  DOI：——

  日期：——