(E)-7,9-decadienoic acid | 302921-10-4

• 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: (E)-7,9-decadienoic acid
• 英文别名: 7,9-Decadienoic acid；(7E)-deca-7,9-dienoic acid
• CAS: 302921-10-4
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: XIHMVGZKONUSLB-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基丁醇 、 (E)-7,9-decadienoic acid 在 N,N'-二环己基碳二亚胺 作用下， 生成 2-methylbutyl (E)-7,9-decadienoate
  参考文献：
  名称：

  摘要：

  This study was undertaken to identify sex pheromone components of nettle caterpillars Darna trima and Darna bradleyi (Lepidoptera: Limacodidae) whose larvae defoliate oil palm, Elaeis guineensis, in southeast Asia. Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone gland extracts revealed two antennally active compounds produced by female D. trima and two by female D. bradleyi. Molecular structures of these candidate pheromone components were identified by electron-impact and chemical-ionization mass spectrometry; retention-index calculations on DB-5, DB-23, and DB-210 columns; microanalytical treatments, as well as syntheses of "auxilliary" compounds that facilitated identification of the compounds. The compounds from D. trima were 2-methylbutyl (E)-7,9-decadienoate (A) and (E)-2-hexenyl (E)-7,9-decadienoate (B); from D. bradleyi we identified methyl (E)-7,9-decadienoate (C), and isobutyl (E)-7,9-decadienoate (D). In field experiments in Malaysia, (S)-2-methylbutyl (E)-7,9-decadienoate (SA) in combination with B proved to be essential and synergistic pheromone components for attraction of male D. trima. (R)-2-Methylbutyl (E)-7,9-decadienoate (RA) had no behavioral activity. Compound D singly attracted male D. bradleyi, but addition of C to D at a 1:10 ratio significantly enhanced attractiveness of the bait. Synthetic pheromone blends were more effective trap baits than unmated female moths and could be developed for monitoring populations of D. trima and D. bradleyi in Asian oil palm plantations.

  DOI：

  10.1023/a:1005561127155
• 作为产物：
  描述：

  (7E)-7,9-癸二烯-1-醇 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-7,9-decadienoic acid
  参考文献：
  名称：

  摘要：

  This study was undertaken to identify sex pheromone components of nettle caterpillars Darna trima and Darna bradleyi (Lepidoptera: Limacodidae) whose larvae defoliate oil palm, Elaeis guineensis, in southeast Asia. Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone gland extracts revealed two antennally active compounds produced by female D. trima and two by female D. bradleyi. Molecular structures of these candidate pheromone components were identified by electron-impact and chemical-ionization mass spectrometry; retention-index calculations on DB-5, DB-23, and DB-210 columns; microanalytical treatments, as well as syntheses of "auxilliary" compounds that facilitated identification of the compounds. The compounds from D. trima were 2-methylbutyl (E)-7,9-decadienoate (A) and (E)-2-hexenyl (E)-7,9-decadienoate (B); from D. bradleyi we identified methyl (E)-7,9-decadienoate (C), and isobutyl (E)-7,9-decadienoate (D). In field experiments in Malaysia, (S)-2-methylbutyl (E)-7,9-decadienoate (SA) in combination with B proved to be essential and synergistic pheromone components for attraction of male D. trima. (R)-2-Methylbutyl (E)-7,9-decadienoate (RA) had no behavioral activity. Compound D singly attracted male D. bradleyi, but addition of C to D at a 1:10 ratio significantly enhanced attractiveness of the bait. Synthetic pheromone blends were more effective trap baits than unmated female moths and could be developed for monitoring populations of D. trima and D. bradleyi in Asian oil palm plantations.

  DOI：

  10.1023/a:1005561127155

文献信息

• METHOD FOR PREPARING (7E)-7, 9-DECADIENOATE ESTER
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US20190106374A1

  公开（公告）日：2019-04-11

  One object of the invention is to provide a method for preparing a 9,9-dialkoxy-7-nonynoate ester and (7E)-7,9-decadienoate ester, which are valuable as intermediates. The method for preparing a (7E)-7,9-decadienoate ester (5) comprises at least steps of: hydrolyzing a 9,9-dialkoxy-7-nonenoate ester (2), R 3 O(R 2 O)CHCH═CH(CH 2 ) 5 CO 2 R 1 , to form a (7E)-9-oxo-7-nonenoate ester (3); and subjecting the (7E)-9-oxo-7-nonenoate ester (3) to a Wittig reaction with a triarylphosphonium methylide (4), Ar 3 P═CH 2 , to form the (7E)-7,9-decadienoate ester (5). The 9,9-dialkoxy-7-nonenoate ester may be prepared by, for example, reducing a 9,9-dialkoxy-7-nonynoate ester (1).

  该发明的一个目的是提供一种制备9,9-二烷氧基-7-壬烯酸酯和(7E)-7,9-癸二烯酸酯的方法，这些化合物作为中间体具有很高的价值。制备(7E)-7,9-癸二烯酸酯(5)的方法至少包括以下步骤：水解9,9-二烷氧基-7-壬烯酸酯(2)，R3O(R2O)CHCH═CH(CH2)5CO2R1，形成(7E)-9-氧代-7-壬烯酸酯(3)；将(7E)-9-氧代-7-壬烯酸酯(3)与三芳基膦甲烯基化合物(4)，Ar3P═CH2，进行威蒂格反应，形成(7E)-7,9-癸二烯酸酯(5)。可以通过还原9,9-二烷氧基-7-壬炔酸酯(1)来制备9,9-二烷氧基-7-壬烯酸酯。
• Method for preparing (7E)-7, 9-decadienoate ester
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US10442752B2

  公开（公告）日：2019-10-15

  One object of the invention is to provide a method for preparing a 9,9-dialkoxy-7-nonynoate ester and (7E)-7,9-decadienoate ester, which are valuable as intermediates. The method for preparing a (7E)-7,9-decadienoate ester (5) comprises at least steps of: hydrolyzing a 9,9-dialkoxy-7-nonenoate ester (2), R3O(R2O)CHCH═CH(CH2)5CO2R1, to form a (7E)-9-oxo-7-nonenoate ester (3); and subjecting the (7E)-9-oxo-7-nonenoate ester (3) to a Wittig reaction with a triarylphosphonium methylide (4), Ar3P═CH2, to form the (7E)-7,9-decadienoate ester (5). The 9,9-dialkoxy-7-nonenoate ester may be prepared by, for example, reducing a 9,9-dialkoxy-7-nonynoate ester (1).

  本发明的一个目的是提供一种制备 9,9-二烷氧基-7-壬炔酸酯和 (7E)-7,9-癸二烯酸酯的方法，它们是有价值的中间体。制备(7E)-7,9-癸二烯酸酯（5）的方法至少包括以下步骤：水解9,9-二烷氧基-7-壬烯酸酯（2），R3O(R2O)CHCH═CH(CH2)5CO2R1，形成(7E)-9-氧代-7-壬烯酸酯（3）；将(7E)-9-氧代-7-壬烯酸酯(3)与三芳基甲基鏻(4)Ar3P═CH2进行维蒂希反应，生成(7E)-7,9-癸二烯酸酯(5)。9,9-二烷氧基-7-壬烯酸酯可通过还原 9,9-二烷氧基-7-壬烯酸酯 (1) 等方法制备。
• HUDLICKY T.; SHETH J. P., TETRAHEDRON LETT., 1979, NO 29, 2667-2670
  作者：HUDLICKY T.、 SHETH J. P.

  DOI：——

  日期：——
• Method for making a coating composition
  申请人：BASF SE

  公开号：EP1268930B1

  公开（公告）日：2009-09-09
• PHARMACEUTICAL COMPOSITION AND METHODS
  申请人：Lipocine Inc.

  公开号：EP3185873A1

  公开（公告）日：2017-07-05