(Z)-12-tetradecen-1-ol | 70711-48-7

• 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: (Z)-12-tetradecen-1-ol
• 英文别名: (Z)-12-Tetradecenol；Z-12-Tetradecen-1-ol；(Z)-tetradec-12-en-1-ol
• CAS: 70711-48-7
• 化学式: C₁₄H₂₈O
• 分子量: 212.376
• InChiKey: IFNFLRVTYVLZAP-IHWYPQMZSA-N

物化性质

• 沸点：
  280.7±8.0 °C(Predicted)
• 密度：
  0.846±0.06 g/cm3(Predicted)
• 保留指数：
  1678.1

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-12-tetradecen-1-ol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (Z)-12-Tetradecenoic acid
  参考文献：
  名称：

  亚洲玉米螟Ostrinia furnacalis 用于信息素生物合成的乙酰转移酶和还原酶系统的底物特异性。

  摘要：

  通过局部应用信息素腺体的前体，在体内研究了乙酰转移酶和还原酶系统在信息素生物合成中使用的 Ostrinia furnacalis (Lepidoptera: Pyralidae) 的底物特异性。每个十四烯醇，双键位置（从 7 到 13）和双键的几何形状不同，都被乙酰转移酶转化为相应的乙酸盐。所有测试的脂肪醇转化率的相似性表明乙酰转移酶具有低底物特异性。大多数相应的十四碳烯酸也可以转化为相应的乙酸酯。然而，测试的脂肪酸之间非常不同的转化率表明还原酶系统比乙酰转移酶具有更高的底物特异性。大多数 E 异构体的转化率高于相应的 Z 异构体的转化率，但 (Delta)-11-十四碳烯酸除外，其中更多的 Z 异构体转化为产物。饱和十四烷酸以高速率转化为相应的乙酸盐；较短的同系物十三烷酸的转化率较低 (56%)，而较长的同系物十五烷酸和十六烷酸各自的乙酸酯的转化率是微不足道的 (<5%)。本研究的结果表

  DOI：

  10.1007/bf02035148
• 作为产物：
  描述：

  11-溴-1-十一醇 在 Lindlar's catalyst 盐酸 、 正丁基锂 、 氨 、 氢气 、 lithium 、 对甲苯磺酸 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二甲基亚砜 为溶剂， 反应 34.08h， 生成 (Z)-12-tetradecen-1-ol
  参考文献：
  名称：

  Enzymatic Desaturation of Fatty Acids:  Δ¹¹ Desaturase Activity on Cyclopropane Acid Probes

  摘要：

  The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3-5 has been investigated using the Delta(11) desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Delta(11) desaturase substrate binding domain is provided considering the cyclopropyl probes 3-5 as conformationally restricted analogues of the straight-chain substrates.

  DOI：

  10.1021/jo0267100

文献信息

• 一种制备(Z ,E)-12-十四碳烯-1-醇乙酸酯的改进方法
  申请人：山东省农药科学研究院

  公开号：CN112574032A

  公开（公告）日：2021-03-30

  本发明提供一种制备(Z,E)‑12‑十四碳烯‑1‑醇乙酸酯的改进方法，wittig反应中的溶剂体系，创新地引入三溶剂体系，增加试剂在反应体系的溶解度，降低溶剂整体凝固点，双重作用下避免反应过程中在较低温度下出现团聚现象，避免反应搅拌不畅和产生大量杂质，进而加大后处理难度；用冰乙酸终止反应，代替之前的含水稀酸，控制原料中剩余的醛类的缩合，避免大量杂质产生，缩合产物一旦产生对三苯氧膦和主产物烯醇溶解度较大，且分离不开，会极大加强后处理难度，产物提取损失大；同时由于反应能在0摄氏度左右以均相状态反应，转化彻底，收率大幅提高，后处理简单，副产物三苯氧膦以颗粒状析出，无大量泥状废弃物，无其它固废。
• Substrate specificity of acetyltransferase and reductase enzyme systems used in pheromone biosynthesis by Asian corn borer,Ostrinia furnacalis
  作者：Cheng-Hua Zhao、Fang Lu、Marie Bengtsson、Christer Löfstedt

  DOI：10.1007/bf02035148

  日期：1995.10

  tested fatty alcohols indicated that the acetyltransferase has a low substrate specificity. Most of the corresponding tetradecenoic acids could also be converted to the respective acetates. However, very different conversion rates among the tested fatty acids demonstrated that the reductase system has a higher substrate specificity than the acetyltransferase. The conversion rates of mostE isomers were

  通过局部应用信息素腺体的前体，在体内研究了乙酰转移酶和还原酶系统在信息素生物合成中使用的 Ostrinia furnacalis (Lepidoptera: Pyralidae) 的底物特异性。每个十四烯醇，双键位置（从 7 到 13）和双键的几何形状不同，都被乙酰转移酶转化为相应的乙酸盐。所有测试的脂肪醇转化率的相似性表明乙酰转移酶具有低底物特异性。大多数相应的十四碳烯酸也可以转化为相应的乙酸酯。然而，测试的脂肪酸之间非常不同的转化率表明还原酶系统比乙酰转移酶具有更高的底物特异性。大多数 E 异构体的转化率高于相应的 Z 异构体的转化率，但 (Delta)-11-十四碳烯酸除外，其中更多的 Z 异构体转化为产物。饱和十四烷酸以高速率转化为相应的乙酸盐；较短的同系物十三烷酸的转化率较低 (56%)，而较长的同系物十五烷酸和十六烷酸各自的乙酸酯的转化率是微不足道的 (<5%)。本研究的结果表
• ——
  作者：J. STEVEN McELFRESH、JOCELYN G. MILLAR、DANIEL RUBINOFF

  DOI：10.1023/a:1010310204552

  日期：——

  The Iepidopteran genus Saturnia has three representatives in North America, S. walterorum, S.mendocino, and S. albofasciata. (E4,Z9)-Tetradecadienal (E4,Z9-14 : Ald) was identified as a sex pheromone component for all three species by combinations of coupled gas chromatography-electroantennogram detection (GC-EAD), GC-mass spectrometry (MS), and field trials. In field trials, all three species were strongly attracted to (E4,Z9-14 : Ald) as a single component. Small amounts of (Z)-9-tetradecenal (Z9-14: Ald) also were found in extracts of all three species, but blends of this compound with E4,Z9-14 : Aid were no more attractive to male moths than E4,Z9-14 : Aid alone. Extracts of pheromone glands of female S. walterorum occasionally contained a third, trace compound eliciting responses from male antennae in GC-EAD experiments, but this compound was not identified. It is suggested that the three species can use the same, single component as a sex attractant because the flight period of S. albofasciata (Fall) is different than that of the other two species (spring), whereas the geographic distributions of S. mendocino and S. walterorum overlap over only small portions of their ranges. Furthermore, the latter two species readily hybridize, so there may be minimal fitness cost to cross-attraction.
• Enzymatic Desaturation of Fatty Acids:  Δ¹¹ Desaturase Activity on Cyclopropane Acid Probes
  作者：Gemma Villorbina、Lidia Roura、Francisco Camps、Jesús Joglar、Gemma Fabriàs

  DOI：10.1021/jo0267100

  日期：2003.4.1

  The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3-5 has been investigated using the Delta(11) desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Delta(11) desaturase substrate binding domain is provided considering the cyclopropyl probes 3-5 as conformationally restricted analogues of the straight-chain substrates.