(10E,12E)-10,12-Tetradecadiensaeure-methylester | 80625-84-9

• 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: (10E,12E)-10,12-Tetradecadiensaeure-methylester
• 英文别名: methyl-(E,E)-10,12-tetradecadienoate；methyl (10E,12E)-tetradeca-10,12-dienoate
• CAS: 80625-84-9
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: AOJHAXBDXKDCAX-VNKDHWASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  17.0
• 可旋转键数：
  10.0
• 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

• 作为产物：
  描述：

  2-[(10-溴癸基)氧基]四氢-2H-吡喃 在 chromium(VI) oxide 、 硫酸 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 36.5h， 生成 (10E,12E)-10,12-Tetradecadiensaeure-methylester
  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

文献信息

• Pheromone XXXIV. Synthese konjugiert-ungesättigter Lepidopterenpheromone und Analoga
  作者：Hans Jürgen Bestmann、Joachim Süß、Otto Vostrowsky

  DOI：10.1002/jlac.198119811205

  日期：1981.12.24

  Nach Art eines “Baukastensystems” werden konjugiert-ungesättigte Alkadienylacetate, Alkadienole und Alkadienale, wie sie als Sexualpheromone weiblicher Schmetterlinge bekannt sind, mit unterschiedlichen Positionen und Geometrien der Doppelbindungen synthetisiert.

  以“模块系统”的方式，合成了共轭-不饱和乙酸链二烯基乙酸酯，链二烯醇和链二烯醛，它们被称为雌性蝴蝶的性信息素，其双键的位置和几何结构不同。
• Identification and biosynthesis of (E,E)-10,12-tetradecadienyl acetate in Spodoptera littoralis female sex pheromone gland
  作者：Isabel Navarro、Esther Mas、Gemma Fabriàs、Francisco Camps

  DOI：10.1016/s0968-0896(97)00072-2

  日期：1997.7

  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.