9,11,13-十四碳三烯-1-醇,(E,E)- | 139061-49-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 9,11,13-十四碳三烯-1-醇,(E,E)-
• 英文名称: (E,E)-9,11,13-tetradecatrienol
• 英文别名: (9E,11E)-tetradeca-9,11,13-trien-1-ol
• CAS: 139061-49-7
• 化学式: C₁₄H₂₄O
• 分子量: 208.344
• InChiKey: ISALVHMRHHEIHZ-VNKDHWASSA-N

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：

  9,11,13-十四碳三烯-1-醇,(E,E)- 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (9E,11E)-9,11,13-tetradecatrienal
  参考文献：
  名称：

  Stereospecific Synthesis of (E,E)-9, 11, 13-Tetradecatrienyl Acetate and Aldehyde (Geometrical Isoers of the Major Components of Two Sex Pheromones of Lepidoptera)

  摘要：

  A stereospecific synthesis of (E,E)-9,11,13-tetradecatrienyl acetate and aldehyde is described. The key steps are two sequential palladium-catalyzed cross-coupling reactions between adequate organometalic reagents and the (E)-1,2-dibromethylene.

  DOI：

  10.1080/00397919108021587
• 作为产物：
  描述：

  1-terbutoxy-9-decyne 在 氢氧化钾 、 四(三苯基膦)钯 、 三氯化铁 、 二异丁基氢化铝 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 32.0h， 生成 9,11,13-十四碳三烯-1-醇,(E,E)-
  参考文献：
  名称：

  Stereospecific Synthesis of (E,E)-9, 11, 13-Tetradecatrienyl Acetate and Aldehyde (Geometrical Isoers of the Major Components of Two Sex Pheromones of Lepidoptera)

  摘要：

  A stereospecific synthesis of (E,E)-9,11,13-tetradecatrienyl acetate and aldehyde is described. The key steps are two sequential palladium-catalyzed cross-coupling reactions between adequate organometalic reagents and the (E)-1,2-dibromethylene.

  DOI：

  10.1080/00397919108021587

文献信息

• Method for Producing Aldehyde and Ketone
  申请人：Yamashita Miyoshi

  公开号：US20110282102A1

  公开（公告）日：2011-11-17

  Provided is a highly efficient method for the production of aldehydes and ketones, which is inexpensive, exhibits high reactivity, and is capable of easy separation of byproduct after the reaction. More particularly, there is provided a method for producing an aldehyde or a ketone, comprising at least an oxidation step of oxidizing a primary alcohol or a secondary alcohol in the presence of a polymeric carbodiimide represented by the following formula (1) and having a weight-average molecular weight of 300 to 5000, and a sulfoxide compound, together with an acid and a base, or together with a salt of the acid and the base.

  提供了一种高效的生产醛和酮的方法，该方法廉价、具有高反应性，并能够在反应后轻松分离副产物。更具体地，提供了一种生产醛或酮的方法，包括至少一个氧化步骤，即在聚合物碳二亚胺（表示为以下式（1）且具有分子量为300至5000的重均分子量）和亚砜化合物的存在下氧化一级醇或二级醇，以及酸和碱，或者酸和碱的盐。
• 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。
• Method for producing aldehyde and ketone
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP2386535A1

  公开（公告）日：2011-11-16

  Provided is a highly efficient method for the production of aldehydes and ketones, which is inexpensive, exhibits high reactivity, and is capable of easy separation of byproduct after the reaction. More particularly, there is provided a method for producing an aldehyde or a ketone, comprising at least an oxidation step of oxidizing a primary alcohol or a secondary alcohol in the presence of a polymeric carbodiimide represented by the following formula (1) and having a weight-average molecular weight of 300 to 5000, and a sulfoxide compound, together with an acid and a base, or together with a salt of the acid and the base.          R1―N=C=N―(R3―N=C=N)―nR2     (1)

  本发明提供了一种生产醛和酮的高效方法，该方法成本低廉，反应活性高，且反应后的副产物易于分离。更具体地说，本发明提供了一种生产醛或酮的方法，该方法至少包括一个氧化步骤，即在由下式（1）表示的、重量平均分子量为 300 至 5000 的聚合物碳二亚胺和亚砜化合物以及酸和碱或酸和碱的盐的存在下，氧化伯醇或仲醇。 R1-N=C=N-(R3-N=C=N)-nR2 (1)
• 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。