(10S,14S)-10,14-dimethyl-1-octadecene | 230973-20-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (10S,14S)-10,14-dimethyl-1-octadecene
• 英文别名: (10S,14S)-10,14-dimethyloctadec-1-ene；10S,14S-dimethyloctadec-1-ene；10S,14S-Dimethyl-1-octadecene
• CAS: 230973-20-3
• 化学式: C₂₀H₄₀
• 分子量: 280.538
• InChiKey: HNNJJUHEQQKTEO-PMACEKPBSA-N

物化性质

• 沸点：
  344.9±9.0 °C(Predicted)
• 密度：
  0.791±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (10S,14S)-10,14-dimethyl-1-octadecene 在 platinum(IV) oxide 氢气 作用下， 以 正己烷 为溶剂， 反应 24.0h， 生成 (5S,9S)-5,9-Dimethyloctadecane
  参考文献：
  名称：

  Synthesis of All the Stereoisomers of 10,14‐Dimethyloctadec‐1‐ene, 5,9‐Dimethyloctadecane and 5,9‐Dimethylheptadecane, the Sex Pheromone Components of the Apple Leafminer, Lyonetia prunifoliella

  摘要：

  All of the stereoisomers of 10,14-dimethyloctadec-1-ene (1), 5,9-dimethyloctadecane (2) and 5,9-dimethylheptadecane (3), the sex pheromone components of the apple leafminer (Lyonetia prunifoliella), were synthesized by starting from the enantiomers of citronellol (4) and methyl 3-hydroxy-2-methylpropanoate (11).

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<973::aid-ejoc973>3.0.co;2-#
• 作为产物：
  描述：

  8-hydroxy-(3R,7R)-3,7-dimethyloctanoic acid 在 吡啶 、 三甲基氯硅烷 、 二异丁基氢化铝 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 38.5h， 生成 (10S,14S)-10,14-dimethyl-1-octadecene
  参考文献：
  名称：

  对映体纯类异戊二烯结构单元的催化不对称合成：在苹果除叶剂信息素的合成中的应用。

  摘要：

  开发了第一个能够制备通用饱和异戊二烯结构单元的所有4种非对映异构体（ee> 99％，de> 98％）的催化不对称方法，并证明了该新方法在将其简单合成为两种方法中的应用价值信息素。

  DOI：

  10.1039/b419268k

文献信息

• Enantiospecific synthesis and filed evaluation of four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component secreted by female moths of the apple leafminer
  作者：Tomonori Taguri、Katuhiko Yaginuma、Masanobu Yamamoto、Toru Fujii、Tetsu Ando

  DOI：10.1080/09168451.2014.905187

  日期：2014.5.4

  All four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component of the apple leafminer (Lyonetia prunifoliella: Lepidoptera), were synthesized starting from (R)- and (S)-propylene oxide by applying stereospecific inversion of chiral secondary tosylates as a key step. Field evaluation showed that male moths of the Japanese population were selectively attracted by the (10S,14S)-isomer

  10,14-二甲基十八烷基-1-烯（苹果除叶剂（Lyonetia prunifoliella：鳞翅目）的性信息素成分）的所有四种立体异构体都是通过（R）-和（S）-环氧丙烷通过应用手性立体定向转化而合成的次要甲苯磺酸盐是关键步骤。田间评估表明，日本种群的雄蛾被（10S，14S）异构体选择性吸引，而对映体未抑制其活性。
• Asymmetric synthesis of the sex pheromone of the apple leafminer, <i>Lyonetia prunifoliella</i>
  作者：Shihang Yu、Gucheng Yuan、Jiawei Liu、Qinghua Bian、Min Wang、Jiangchun Zhong

  DOI：10.1002/chir.23524

  日期：2023.2

  Lyonetia prunifoliella is a significant pest in orchards and damages apple. The sex pheromones of this pest were prepared via a new and concise method. The central to our method were Evans' chiral auxiliaries, the addition of chiral Grignard reagent to aldehyde and Wittig coupling.

  Lyonetia prunifoliell a 是果园的重要害虫，为害苹果。这种害虫的性信息素是通过一种新的、简洁的方法制备的。我们方法的核心是 Evans 的手性助剂，将手性格氏试剂添加到醛和 Wittig 偶联中。
• Synthesis of the Enantiomers ofanti-2,6-Dimethylheptane-1,7-diol Monotetrahydropyranyl Ether and Their Conversion into the Enantiomers of the Sex Pheromone Components of the Apple Leafminer,Lyonetia prunifoliella
  作者：Yoshihide Nakamura、Kenji Mori

  DOI：10.1002/1099-0690(200008)2000:15<2745::aid-ejoc2745>3.0.co;2-i

  日期：2000.8

  Both (2R,6R)- and (2S,6S)-isomers of 2,6-dimethylheptane-1,7-diol monotetrahydropyranyl ether (4) were synthesized, and converted into the enantiomers of anti-10,14-dimethyl-1-octadecene (1), anti-5,9-dimethyloctadecane (2) and anti-5,9-dimethylheptadecane (3), the sex pheromone components of the apple leaf miner (Lyonetia prunifoliella).
• Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: application in the synthesis of apple leafminer pheromones
  作者：Ruben P. van Summeren、Sven J. W. Reijmer、Ben L. Feringa、Adriaan J. Minnaard

  DOI：10.1039/b419268k

  日期：——

  The first catalytic asymmetric procedure capable of preparing all 4 diastereoisomers (ee > 99%, de > 98%) of a versatile saturated isoprenoid building block was developed and the value of this new method was demonstrated in its application to the concise total synthesis of two pheromones.

  开发了第一个能够制备通用饱和异戊二烯结构单元的所有4种非对映异构体（ee> 99％，de> 98％）的催化不对称方法，并证明了该新方法在将其简单合成为两种方法中的应用价值信息素。
• Synthesis of All the Stereoisomers of 10,14‐Dimethyloctadec‐1‐ene, 5,9‐Dimethyloctadecane and 5,9‐Dimethylheptadecane, the Sex Pheromone Components of the Apple Leafminer, <i>Lyonetia</i> <i>prunifoliella</i>
  作者：Hideki Tamagawa、Hirosato Takikawa、Kenji Mori

  DOI：10.1002/(sici)1099-0690(199905)1999:5<973::aid-ejoc973>3.0.co;2-#

  日期：1999.5

  All of the stereoisomers of 10,14-dimethyloctadec-1-ene (1), 5,9-dimethyloctadecane (2) and 5,9-dimethylheptadecane (3), the sex pheromone components of the apple leafminer (Lyonetia prunifoliella), were synthesized by starting from the enantiomers of citronellol (4) and methyl 3-hydroxy-2-methylpropanoate (11).