(10S,14R)-10,14-dimethyl-1-octadecene | 230973-21-4

• 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,14R)-10,14-dimethyl-1-octadecene
• 英文别名: 10S,14R-dimethyloctadec-1-ene；(10S,14R)-10,14-dimethyloctadec-1-ene
• CAS: 230973-21-4
• 化学式: C₂₀H₄₀
• 分子量: 280.538
• InChiKey: HNNJJUHEQQKTEO-UXHICEINSA-N

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,14R)-10,14-dimethyl-1-octadecene 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 臭氧 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 29.0h， 生成 5R,9S-dimethylheptadecane
  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：

  magnesium,hex-1-ene,bromide 在 六甲基磷酰三胺 、 氢氧化钾 、 Li₂CuBr₂SMe₂SPh 、 三乙基硼氢化锂 、 magnesium 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 77.0h， 生成 (10S,14R)-10,14-dimethyl-1-octadecene
  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-#

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。
• 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).