(5S,9S)-5,9-Dimethylheptadecane | 108195-53-5

• 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-Dimethylheptadecane
• 英文别名: 5S,9S-dimethylheptadecane
• CAS: 108195-53-5；121723-03-3；121723-04-4；121723-05-5；121723-06-6
• 化学式: C₁₉H₄₀
• 分子量: 268.527
• InChiKey: NAZZVMQIBMVGND-OALUTQOASA-N

物化性质

• 沸点：
  83 °C(Press: 0.8 Torr)
• 密度：
  0.783±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  19
• 可旋转键数：
  14
• 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：

  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 (5S,9S)-5,9-Dimethylheptadecane
  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

• 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：——
• Stereospecific inversion of secondary tosylates to yield chiral methyl-branched building blocks, applied to the asymmetric synthesis of leafminer sex pheromones
  作者：Tomonori Taguri、Rei Yamakawa、Toru Fujii、Yuta Muraki、Tetsu Ando

  DOI：10.1016/j.tetasy.2012.05.023

  日期：2012.6

  All four of the possible stereoisomers of 5,9-dimethylheptadecane, the major sex pheromone component secreted by female moths of the mountain-ash bentwing (Leucoptera scitella), were synthesized by the coupling of two chiral blocks with a methyl branch at the 2- or 3-position. The blocks were prepared by applying the stereospecific inversion of secondary tosylates, which were derived from (R)- and (S)-propylene oxide, and their enantiopurities were confirmed by chiral HPLC analysis. (c) 2012 Elsevier Ltd. All rights reserved.
• 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).
• 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).