methyl-9,11-tetradecadiynoate | 194926-15-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl-9,11-tetradecadiynoate
• 英文别名: methyl tetradeca-9,11-diynoate
• CAS: 194926-15-3
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: AWBUURSYEBFPIA-UHFFFAOYSA-N

物化性质

• 沸点：
  337.5±25.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl-9,11-tetradecadiynoate 在 copper diacetate 、 silver nitrate 、 锌 作用下， 以 甲醇 、 水 为溶剂， 以30%的产率得到methyl-(Z,Z)-9,11-tetradecadienoate
  参考文献：
  名称：

  Identification and biosynthesis of (E,E)-10,12-tetradecadienyl acetate in Spodoptera littoralis female sex pheromone gland

  摘要：

  A minor component of the sex pheromone gland of the Egyptian cotton leafworm, Spodoptera littoralis, has been identified as (E,E)-10,12-tetradecadienyl acetate. Structural elucidation has been carried out by isobutane-chemical ionization mass spectrometry of the fatty acyl biosynthetic precursor-derived methyl ester. To assign the stereochemistry of the double bonds, the four isomers of both 10,12-tetradecadienyl acetates and methyl 10,12-tetradecadienoates have been synthesized and their gas chromatography retention times and mass spectra have been compared to those of the corresponding natural compounds. Mass-labeling experiments showed that the (E,E)-10,12-tetradecadienoyl moiety is biosynthetically derived from (Z)-11-tetradecenoic acid in the insect pheromone gland. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00072-2
• 作为产物：
  描述：

  10-(methoxymethoxy)-1-decyne 在 盐酸 、 甲醇 、 正丙胺 、 copper(l) iodide 、 重铬酸吡啶 、 盐酸羟胺 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 methyl-9,11-tetradecadiynoate
  参考文献：
  名称：

  Identification and biosynthesis of (E,E)-10,12-tetradecadienyl acetate in Spodoptera littoralis female sex pheromone gland

  摘要：

  A minor component of the sex pheromone gland of the Egyptian cotton leafworm, Spodoptera littoralis, has been identified as (E,E)-10,12-tetradecadienyl acetate. Structural elucidation has been carried out by isobutane-chemical ionization mass spectrometry of the fatty acyl biosynthetic precursor-derived methyl ester. To assign the stereochemistry of the double bonds, the four isomers of both 10,12-tetradecadienyl acetates and methyl 10,12-tetradecadienoates have been synthesized and their gas chromatography retention times and mass spectra have been compared to those of the corresponding natural compounds. Mass-labeling experiments showed that the (E,E)-10,12-tetradecadienoyl moiety is biosynthetically derived from (Z)-11-tetradecenoic acid in the insect pheromone gland. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00072-2