(5S,9S)-5,9-Dimethyloctadecane | 131906-86-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 英文名称: (5S,9S)-5,9-Dimethyloctadecane
• 英文别名: 5S,9S-dimethyloctadecane
• CAS: 131906-86-0
• 化学式: C₂₀H₄₂
• 分子量: 282.553
• InChiKey: MEHFAVZCNHHAMJ-PMACEKPBSA-N

物化性质

• 沸点：
  325.2±9.0 °C(Predicted)
• 密度：
  0.786±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：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (S)-1-bromo-2-methylhexane 在 platinum(IV) oxide 氢气 、 三乙基硼氢化锂 、 magnesium 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 为溶剂， 反应 82.5h， 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-#

文献信息

• 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。
• Mori, Kenji; Wu, Jiang, Liebigs Annalen der Chemie, 1991, # 5, p. 439 - 444
  作者：Mori, Kenji、Wu, Jiang

  DOI：——

  日期：——
• 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).
• MORI, KENJI;WU, JIANG, LIEBIGS ANN. CHEM.,(1991) N, C. 439-443
  作者：MORI, KENJI、WU, JIANG

  DOI：——

  日期：——
• 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).