(6S)-2,6-Dimethyl-2-decene | 171627-78-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (6S)-2,6-Dimethyl-2-decene
• 英文别名: (S)-2,6-dimethyl-2-decene；2,6-dimethyl-2-decene；(6S)-2,6-dimethyldec-2-ene
• CAS: 171627-78-4
• 化学式: C₁₂H₂₄
• 分子量: 168.323
• InChiKey: YRZOHUILUXHAJX-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (6S)-2,6-Dimethyl-2-decene 在 potassium permanganate 、 2,3-二巯基丁二酸 、 臭氧 作用下， 生成 (4S)-4-methyloctanoic acid
  参考文献：
  名称：

  Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae)

  摘要：

  Male coconut minoceros beetles, Oryctes rhinoceros (L.), produce three sex-specific compounds, ethyl 4-methyloctanoate, ethyl 4-methylheptanoate, and 4-methyloctanoic acid, the first of which is an aggregation pheromone. Synthesis of these compounds involving conjugate addition of organocuprates to ethyl acrylate is reported. In field trapping experiments, (4S)-ethyl-4-methyloctanoate and the racemic mixture were equally attractive and 10 times more effective in attracting beetles than ethyl chrysanthemumate, a previously recommended attractant. Ethyl 4-methylheptanoate was as attractive as ethyl chrysanthemumate and more attractive than 4-methyloctanoic acid, but further studies are required before it can be classed as an aggregation pheromone. Compared to ethyl 4-methyloctanoate alone, combinations of the three male-produced compounds did not increase attraction, whereas addition of freshly rotting oil palm fruit bunches to pheromone-baited traps significantly enhanced attraction. With increasing dose, captures of O. rhinoceros increased, but doses of 6, 9, and 18 mg/day were competitive with 30 mg/day lures. Newly designed vane traps were more effective in capturing beetles than were barrier or pitfall traps. Results of this study indicate that there is potential for using ethyl 4-methyloctanoate in operational programs to control O. rhinoceros in oil palm plantations.

  DOI：

  10.1007/bf02035152
• 作为产物：
  描述：

  (R)-(+)-β-香茅醇 在 吡啶 、 dilithium tetrachlorocuprate 、 magnesium 作用下， 反应 24.0h， 生成 (6S)-2,6-Dimethyl-2-decene
  参考文献：
  名称：

  信息素合成，CLXXVI。3,13-二甲基十七烷的四种立体异构体的合成，这是西方假铁杉回路的主要性信息素成分†

  摘要：

  从香茅醇（2a）和2-甲基-1的对映体开始合成了3,13-二甲基庚烷（1）的所有四种立体异构体，它们是西方虚假铁杉弯钩虫（Nepytia freemani）的雌性产生的性信息素。-丁醇（4a）。

  DOI：

  10.1002/jlac.199619961205

文献信息

• Synthesis of the Enantiomers of Some Methyl-branched Cuticular Hydrocarbons of the Ant, Diacamma sp.
  作者：Kaoru MARUKAWA、Hirosato TAKIKAWA、Kenji MORI

  DOI：10.1271/bbb.65.305

  日期：2001.1

  The enantiomers of 3-methylpentacosane, 3-methylheptacosane, 3-methylnonacosane, 13-methylheptacosane, and 5-methylheptacosane were synthesized by starting from the enantiomers of 2-methylbutyl bromide or citronellol. These methyl-branched alkanes are the characteristic components of the cuticular hydrocarbons of queen of the ant, Diacamma sp.

  3-甲基二十五烷、3-甲基二十七烷、3-甲基二十九烷、13-甲基二十七烷和5-甲基二十七烷的对映体是通过从2-甲基丁基溴或香茅醇的对映体开始合成的。这些甲基分支的烷烃是蚁后体表角质层碳氢化合物的特征成分，来自蚁属Diacamma。
• Pheromone synthesis. Part 258. Synthesis of the enantiomers of the beetle pheromones ethyl 4-methylheptanoate, 4-methyloctanoic acid and 4-methyl-1-nonanol, and HPLC analysis of their derivatives to determine their enantiomeric purities
  作者：Kenji Mori、Kazuaki Akasaka

  DOI：10.1016/j.tetasy.2016.01.014

  日期：2016.3

  The enantiomers of citronella) have been converted into the enantiomers of the following beetle Pheromones: ethyl 4-methylheptanoate (produced by male Nicrophorus vespilloides), 4-methyloctanoic acid (produced by male Oryctes elegans), and 4-methyl-1-nonanol (produced by female Tenebrio molitor). The enantiomeric purities of the synthetic pheromones were determined by HPLC analysis of the corresponding acids after derivatization with Ohrui's reagent [(S)-1-(anthracene-2,3-dicarboximido)-2-propanol]. The enantiomers of 4-methyl-1-nonanol could also be analyzed employing another Ohrui's reagent [(1S,2S)-2-(naphthalene-2,3-dicarboximido)cyclohexane-l-carboxylic acid]. (C) 2016 Elsevier Ltd. All rights reserved.
• Pheromone Synthesis, CLXXVI. Synthesis of the Four Stereoisomers of 3,13-Dimethylheptadecane, the Major Sex Pheromone Component of the Western False Hemlock Looper
  作者：Hirosato Takikawa、Yasuo Shirai、Makoto Kobayashi、Kenji Mori

  DOI：10.1002/jlac.199619961205

  日期：1996.12

  All of the four stereoisomers of 3,13-dimethylheptadecane (1), the female-produced sex pheromone of the western false hemlock looper (Nepytia freemani), were synthesized by starting from the enatiomers of citronellol (2a) and 2-methyl-1-butanol (4a).

  从香茅醇（2a）和2-甲基-1的对映体开始合成了3,13-二甲基庚烷（1）的所有四种立体异构体，它们是西方虚假铁杉弯钩虫（Nepytia freemani）的雌性产生的性信息素。-丁醇（4a）。
• Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae)
  作者：Rebecca H. Hallett、Alice L. Perez、Gerhard Gries、Regine Gries、Harold D. Pierce、Junming Yue、A. Cameron Oehlschlager、Lilliana M. Gonzalez、John H. Borden

  DOI：10.1007/bf02035152

  日期：1995.10

  Male coconut minoceros beetles, Oryctes rhinoceros (L.), produce three sex-specific compounds, ethyl 4-methyloctanoate, ethyl 4-methylheptanoate, and 4-methyloctanoic acid, the first of which is an aggregation pheromone. Synthesis of these compounds involving conjugate addition of organocuprates to ethyl acrylate is reported. In field trapping experiments, (4S)-ethyl-4-methyloctanoate and the racemic mixture were equally attractive and 10 times more effective in attracting beetles than ethyl chrysanthemumate, a previously recommended attractant. Ethyl 4-methylheptanoate was as attractive as ethyl chrysanthemumate and more attractive than 4-methyloctanoic acid, but further studies are required before it can be classed as an aggregation pheromone. Compared to ethyl 4-methyloctanoate alone, combinations of the three male-produced compounds did not increase attraction, whereas addition of freshly rotting oil palm fruit bunches to pheromone-baited traps significantly enhanced attraction. With increasing dose, captures of O. rhinoceros increased, but doses of 6, 9, and 18 mg/day were competitive with 30 mg/day lures. Newly designed vane traps were more effective in capturing beetles than were barrier or pitfall traps. Results of this study indicate that there is potential for using ethyl 4-methyloctanoate in operational programs to control O. rhinoceros in oil palm plantations.