(6Z,9Z)-octadeca-6,9-diene | 6114-20-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (6Z,9Z)-octadeca-6,9-diene
• 英文别名: 9,12-Octadecadiene
• CAS: 6114-20-1
• 化学式: C₁₈H₃₄
• 分子量: 250.468
• InChiKey: LWPSUELGZBFZHK-BCTRXSSUSA-N

物化性质

• 熔点：
  -45 °C
• 沸点：
  307 °C
• 密度：
  0.800±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (6Z,9Z)-octadeca-6,9-diene 在 间氯过氧苯甲酸 作用下， 生成 2-Pentyl-3-((Z)-undec-2-enyl)-oxirane 、 (6Z)-9,10-Epoxyoctadecene
  参考文献：
  名称：

  Sex attractants of geometrid and noctuid moths: Chemical characterization and field test of monoepoxides of 6,9-dienes and related compounds

  摘要：

  (Z,Z)-6,9-Dienes with straight C-18-C-23 chains were synthesized from linoleic acid, and a C-17 chain was synthesized by hydrogenation of the corresponding 6,9-diyne prepared from propargyl alcohol. Oxidation of the homoconjugated dienes with m-chloroperoxybenzoic acid yielded a 1:1 mixture of two monoepoxides that could be separated by repeated medium-pressure liquid chromatography with a Lobar column. The chemical structure of each positional isomer was confirmed by analyses of the ozonolysis products, and the isomers showed characteristic C-13 signals in their NMR spectra and fragment ions in their EI mass spectra. In addition to the (Z,Z,Z)-3,6,9-trienes with straight C-18-C-23 chains and their monoepoxides, field tests using single source lures incorporating one of the above seven dienes and 14 monoepoxymonoenes were carried out in a forest in Tokyo from 1992 to 1994. Consequently, attraction of six geometrid species and five noctuid species was observed for the first time.

  DOI：

  10.1007/bf02036719
• 作为产物：
  描述：

  亚油酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 4.5h， 生成 (6Z,9Z)-octadeca-6,9-diene
  参考文献：
  名称：

  Bascetta, Emanuele; Gunstone, Frank D.; Walton, John C., Journal of the Chemical Society. Perkin transactions II, 1983, p. 603 - 614

  摘要：

  DOI：

文献信息

• Cobalt-Catalyzed Decarboxylative Methylation and Ethylation of Aliphatic N-(Acyloxy)phthalimides with Organoaluminum Reagents
  作者：Rui Shang、Yao Fu、Ze-Zhong Wang、Guang-Zu Wang、Bin Zhao

  DOI：10.1055/s-0040-1707946

  日期：2020.7

  A cobalt-catalyzed decarboxylative methylation of aliphatic redox-active esters [N-(acyloxy)phthalimides; RAEs] with trimethylaluminum under mild conditions was developed, providing a method for transforming a carboxylate group into a methyl group without redox fluctuation. Primary and secondary RAEs were both amenable substrates, whereas a tertiary RAE delivered an elimination product. Triethylaluminum

  脂肪族氧化还原活性酯 [N-（酰氧基）邻苯二甲酰亚胺；RAEs] 与三甲基铝在温和条件下的开发，提供了一种将羧酸盐基团转化为甲基基团而没有氧化还原波动的方法。一级和二级 RAE 都是适合的底物，而三级 RAE 提供消除产物。三乙基铝也用于提供脱羧乙基化产物。
• Deoxygenation of triglycerides by silylation under exceptionally mild conditions
  作者：Cody B. Gale、Michael A. Brook

  DOI：10.1039/c8gc01324a

  日期：——

  Efficient deoxygenation of lipids using hydrosiloxanes leads to polyunsaturated hydrocarbons.

  使用氢硅氧烷高效去氧化脂质，可生成多不饱和烃。
• GIUMANINI, ANGELO G.;TUBARO, FRANCO, J. PRAKT. CHEM., 332,(1990) N, C. 755-761
  作者：GIUMANINI, ANGELO G.、TUBARO, FRANCO

  DOI：——

  日期：——
• Bascetta, Emanuele; Gunstone, Frank D.; Walton, John C., Journal of the Chemical Society. Perkin transactions II, 1983, p. 603 - 614
  作者：Bascetta, Emanuele、Gunstone, Frank D.、Walton, John C.

  DOI：——

  日期：——
• Sex attractants of geometrid and noctuid moths: Chemical characterization and field test of monoepoxides of 6,9-dienes and related compounds
  作者：Tetsu Ando、Hideki Kishi、Naoko Akashio、Xu-Rong Qin、Namiko Saito、Hiroshi Abe、Satoshi Hashimoto

  DOI：10.1007/bf02036719

  日期：1995.3

  (Z,Z)-6,9-Dienes with straight C-18-C-23 chains were synthesized from linoleic acid, and a C-17 chain was synthesized by hydrogenation of the corresponding 6,9-diyne prepared from propargyl alcohol. Oxidation of the homoconjugated dienes with m-chloroperoxybenzoic acid yielded a 1:1 mixture of two monoepoxides that could be separated by repeated medium-pressure liquid chromatography with a Lobar column. The chemical structure of each positional isomer was confirmed by analyses of the ozonolysis products, and the isomers showed characteristic C-13 signals in their NMR spectra and fragment ions in their EI mass spectra. In addition to the (Z,Z,Z)-3,6,9-trienes with straight C-18-C-23 chains and their monoepoxides, field tests using single source lures incorporating one of the above seven dienes and 14 monoepoxymonoenes were carried out in a forest in Tokyo from 1992 to 1994. Consequently, attraction of six geometrid species and five noctuid species was observed for the first time.

表征谱图