[13,13,14,14,14-(2)H5]-(Z)-11-tetradecen-1-ol | 199013-40-6

• 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: [13,13,14,14,14-(2)H5]-(Z)-11-tetradecen-1-ol
• 英文别名: (13,13,14,14,14-(2)H5) (Z)-11-tetradecen-1-ol
• CAS: 199013-40-6
• 化学式: C₁₄H₂₈O
• 分子量: 217.336
• InChiKey: YGHAIPJLMYTNAI-KVUODVCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  15.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  [13,13,14,14,14-(2)H5]-(Z)-11-tetradecen-1-ol 在 chromium(VI) oxide 、 RhCl(PPh₃)3 、 硫酸 、 氘 作用下， 以 水 、 苯 为溶剂， 生成 erythro-(11,12,13,13,14,14,14-2H₇)myristic acid
  参考文献：
  名称：

  Stereospecificity of the (E)- and (Z)-11 Myristoyl CoA Desaturases in the Biosynthesis of Spodoptera littoralis Sex Pheromone

  摘要：

  DOI：

  10.1021/ja972577v
• 作为产物：
  描述：

  10-十一炔醇 在 palladium on barium sulfate 喹啉 、 盐酸 、 甲醇 、 甲基锂 、 氢气 、 对甲苯磺酸 、 lithium bromide 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 37.0h， 生成 [13,13,14,14,14-(2)H5]-(Z)-11-tetradecen-1-ol
  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

• Penta-deuterated acid precursors in the pheromone biosynthesis of the Egyptian armyworm,<i>Spodoptera littoralis</i>
  作者：Lourdes Muñoz、Gloria Rosell、Angel Guerrero

  DOI：10.1002/jlcr.1666

  日期：2009.9.30

  Synthesis of penta-deuterated intermediate precursors d5(E)-11-14:Acid (7), d5(Z)-11-14:Acid (10) and d514:Acid (12) of the pheromone of the Egyptian armyworm Spodoptera littoralis has been accomplished by a very convenient route starting from the commercially available 9-dodecyn-1-ol. The processes occur with a high to excellent chemical and stereochemical yields and the compounds have been successfully used in the confirmation of the pheromone composition and biosynthesis of our strain. Copyright © 2009 John Wiley & Sons, Ltd.

  成功合成了一种从商业上可获得的9-dodec炔-1-醇开始的非常便捷途径，得到了埃及棉铃虫Spodoptera littoralis性信息素的重氢化中间体前体d5(E)-11-14:酸(7)、d5(Z)-11-14:酸(10)和d514:酸(12)。该过程在化学和立体化学产率上都非常高至优秀，并且这些化合物已成功用于证实我们菌株的性信息素组成和生物合成。版权所有 © 2009 John Wiley & Sons, Ltd.
• Pheromone differences between sibling taxaDiachrysia chrysitis (linnaeus, 1758) andD. tutti (Kostrowicki, 1961) (Lepidoptera: Noctuidae)
  作者：Christer Löfstedt、Bill S. Hansson、Miklos Tòth、Gabor Szöcs、Vincas Buda、Marie Bengtsson、Nils Ryrholm、Mats Svensson、Ernst Priesner

  DOI：10.1007/bf02065993

  日期：1994.1

  The noctuid sibling taxa Diachrysia chrpsitis s. str. and D. tutti, of yet uncertain taxonomic status, have previously been shown to possess differences in morphology and to be attracted to different mixtures of the two presumed pheromone components (Z)-5-decenyl acetate and (Z)-7-decenyl acetate. Typical D. tutti males (clearly broken forewing marking) are known to respond to a 2:100 mixture of the two isomers, whereas D. chrysitis males (unbroken marking) are attracted to a 100:10 mixture. We investigated female pheromone production and male electroantennographic (EAG) response in Diachrysia families raised in the laboratory from held-collected gravid females. Extracts of individual females from typical D. tutti and D. chrysitis families were subjected to gas chromatography with simultaneous flame ionization and electroantennographic detection. All females produced mixtures of Z5- and Z7-10:OAc, but female D. chrysitis produced predominantly Z5-10:OAc