(7E)-7,9-癸二烯-1-醇 | 302921-09-1

• 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: (7E)-7,9-癸二烯-1-醇
• 英文名称: (7E)-deca-7,9-dien-1-ol
• 英文别名: (E)-7,9-decadien-1-ol
• CAS: 302921-09-1
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: WIIGCNVKVVQGOY-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (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
• 作为产物：
  描述：

  1,7-庚二醇 在 正丁基锂 、 草酰氯 、 四丁基氟化铵 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 7.0h， 生成 (7E)-7,9-癸二烯-1-醇
  参考文献：
  名称：

  Formation of Isomerized E,Z-Configured 1,3-Dienes in Construction of Macrocyclic Trienes by Diene-Ene RCM

  摘要：

  通过四烯的二烯-烯RCM构建大环三烯的研究表明，反应中得到的大环三烯是两种异构体的混合物，这些异构体具有E,Z-配置的1,3-二烯部分。两种异构体的形成可以通过最初生成的钌-烯烃卡宾中间体的E-Z异构化来解释。

  DOI：

  10.1246/bcsj.20140250

文献信息

• Instrumental Analysis of Terminal-Conjugated Dienes for Reexamination of the Sex Pheromone Secreted by a Nettle Moth,<i>Parasa lepida lepida</i>
  作者：MD. Azharul ISLAM、Rei YAMAKAWA、Nguyen Duc DO、Naoko NUMAKURA、Toshiro SUZUKI、Tetsu ANDO

  DOI：10.1271/bbb.90047

  日期：2009.5.23

  Conjugated dienyl compounds make one of the main groups of lepidopteran sex pheromones, and GC has been frequently used to determine the configurations of the double bonds. However, the separation of two geometric isomers of a terminal-conjugated diene, such as 7,9-decadien-1-ol secreted by a nettle moth Parasa lepida lepida (Limacodidae), is assumed to be difficult. In order to clarify the chromatographic separation of the terminal dienes, 7,9-decadienyl and 9,11-dodecadienyl compounds (alcohols, acetates, and aldehydes) were analyzed by GC and HPLC. On a capillary GC column, the (E)-isomers flowed out slightly faster than the corresponding (Z)-isomers, but their peaks almost overlapped. On the other hand, HPLC equipped with an ODS column completely separated the two geometric isomers examined and the (Z)-isomers eluted from the column faster than the (E)-isomers without dependence on a functional group. In addition to undergoing direct HPLC analysis without derivatization, the dienyl alcohols were converted into 3,5-dinitrobenzoates and analyzed by LC-ESI-MS operated under the same reversed-phase condition. The two separated geometric isomers were sensitively monitored by negative ions at m⁄z 211, M, M+1, M+17, and M+31, which were characteristically derived from the benzoates. Based on these results, a pheromone extract of P. l. lepida was examined, and it was confirmed that the female moths exclusively produced the (Z)-isomer of the 7,9-diene. Furthermore, a GC-EAD analysis and a field evaluation with both geometrical isomers indicated that the mating communication of P. l. lepida is predominantly mediated with the (Z)-isomer.

  共轭二烯基化合物是鳞翅目性信息素的主要基团之一，GC 经常用于确定双键的构型。然而，末端共轭二烯的两个几何异构体的分离，例如由荨麻蛾 Parasa lepida lepida (Limacodidae) 分泌的 7,9-decadien-1-ol，被认为是困难的。为了阐明末端二烯的色谱分离，通过 GC 和 HPLC 分析了 7,9-癸二烯基和 9,11-十二二烯基化合物（醇、乙酸酯和醛）。在毛细管气相色谱柱上，(E)-异构体的流出速度略快于相应的(Z)-异构体，但它们的峰几乎重叠。另一方面，配备ODS柱的HPLC完全分离了所检查的两种几何异构体，并且(Z)-异构体从柱中洗脱得比(E)-异构体更快，而不依赖于官能团。除了不进行衍生化直接进行 HPLC 分析外，还将二烯醇转化为 3,5-二硝基苯甲酸酯，并通过在相同反相条件下操作的 LC-ESI-MS 进行分析。通过 m/z 211、M、M+1、M+17 和 M+31 处的负离子灵敏地监测这两种分离的几何异构体，这些异构体通常源自苯甲酸盐。基于这些结果，P. l. 的信息素提取物。对lepida进行了检查，证实雌性蛾只产生7,9-二烯的(Z)-异构体。此外，GC-EAD 分析和对两种几何异构体的现场评估表明，P. l. 的交配通讯。 lepida 主要由 (Z)-异构体介导。
• HALOALKENYL ALKOXYMETHYL ETHER COMPOUND AND A PROCESS FOR PREPARING A TERMINAL CONJUGATED ALKADIEN-1-YL ACETATE COMPOUND AND A TERMINAL CONJUGATED ALKADIEN-1-OL COMPOUND THEREFROM
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP3978464A1

  公开（公告）日：2022-04-06

  The present invention relates to a haloalkenyl alkoxymethyl ether compound of the following general formula (1): R1CH2OCH2OCH2CH2CH=CH(CH2)aX1 (1) wherein R1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X1 represents a halogen atom, and "a" represents an integer of 3 to 14. The present invention also relates to processes for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5): CH2=CHCH=CH(CH2)aOAc (5) wherein "a" is as defined above, and Ac represents an acetyl group, and a terminal conjugated alkadien-1-ol compound of the following general formula (6): CH2=CHCH=CH(CH2)aOH (6) wherein "a" is as defined above, from the haloalkenyl alkoxymethyl ether compound (1).

  本发明涉及下通式(1)的卤代烯基烷氧基甲基醚化合物：R1CH2OCH2OCH2CH2CH=CH(CH2)aX1 (1) 其中 R1 代表氢原子、具有 1 至 9 个碳原子的正烷基或苯基，X1 代表卤素原子，"a "代表 3 至 14 的整数。本发明还涉及制备以下通式（5）的末端共轭烷二烯-1-基乙酸酯化合物的工艺：CH2＝CHCH＝CH(CH2)aOAc(5)，其中 "a "如上定义，Ac 代表乙酰基，以及下通式(6)的末端共轭烷二烯-1-醇化合物：CH2=CHCH=CH(CH2)aOH(6)，其中 "a "如上定义，来自卤代烯基烷氧甲基醚化合物(1)。
• US3993854A
  申请人：——

  公开号：US3993854A

  公开（公告）日：1976-11-23
• US4044195A
  申请人：——

  公开号：US4044195A

  公开（公告）日：1977-08-23
• Formation of Isomerized <i>E</i>,<i>Z</i>-Configured 1,3-Dienes in Construction of Macrocyclic Trienes by Diene-Ene RCM
  作者：Ryukichi Takagi、Kenji Tanaka、Koumei Yamamoto、Yoshikazu Hiraga、Satoshi Kojima、Manabu Abe

  DOI：10.1246/bcsj.20140250

  日期：2015.1.15

  Construction of macrocyclic trienes by diene-ene RCM of tetraenes was examined. In the reactions, macrocyclic trienes were obtained as a mixture of two isomers with E,Z-configured 1,3-diene moiety. The formation of two isomers can be understandable by the E–Z isomerization of the initially generated ruthenium–alkenyl carbene intermediate.

  通过四烯的二烯-烯RCM构建大环三烯的研究表明，反应中得到的大环三烯是两种异构体的混合物，这些异构体具有E,Z-配置的1,3-二烯部分。两种异构体的形成可以通过最初生成的钌-烯烃卡宾中间体的E-Z异构化来解释。