Δ¹¹-tetradecenol | 114052-40-3

• 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: Δ¹¹-tetradecenol
• 英文别名: (Z,E)-tetradec-11-en-1-ol；11-tetradecen-1-ol；11-tetradecenol；Tetradec-11-en-1-ol
• CAS: 114052-40-3
• 化学式: C₁₄H₂₈O
• 分子量: 212.376
• InChiKey: YGHAIPJLMYTNAI-UHFFFAOYSA-N

物化性质

• 熔点：
  35.5°C (estimate)
• 沸点：
  317.23°C (estimate)
• 密度：
  0.8521 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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：

  Δ¹¹-tetradecenol 在 四氮唑 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 phosphoric acid di-tert-butyl ester tetradec-11-enyl ester
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships, and Biological Evaluation of Fatty Alcohol Phosphates as Lysophosphatidic Acid Receptor Ligands, Activators of PPARγ, and Inhibitors of Autotaxin

  摘要：

  We previously reported that fatty alcohol phosphates (FAP) represent a minimal pharmacophore required to interact with lysophosphatidic acid (LPA) receptors. To improve the activity of the first-generation saturated FAP series, a structure-activity relationship (SAR) study was carried out that includes modifications to the headgroup and alkyl side chain of the FAP pharmacophore. A series of unsaturated (C-10-C-18) FAP, headgroup-modified hydrolytically stable saturated (C-10-C-18) alkyl phosphonates, and saturated and unsaturated (C-10-C-18) thiophosphate analogues were synthesized and evaluated for activity in RH7777 cells transfected with individual LPA(1-3) receptors, in PC-3 cells and in human platelets that endogenously express all three isoforms. In this series we identified several LPA(1)- and LPA(3)-selective antagonists with IC50 values in the nanomolar range. Oleoyl-thiophosphate (15g) was shown to be a panagonist, whereas tetradecyl-phosphonate (16c) was identified as a pan-antagonist. These compounds were also tested for the ability to activate the transcription factor PPAR gamma, an intracellular receptor for LPA, in CV1 cells transfected with the PPRE-Acox-Rluc reporter gene. All the FA-P tested, along with the previously reported LPA GPCR antagonists dioctanoyl glycerol pyrophosphate (2), Ki16425 (6), and the agonist OMPT (3), were activators of PPAR gamma. The pan-agonist oleoyl-thiophosphate (15g) and pan-antagonist tetradecyl-phosphonate (16c) mimicked LPA in inhibiting autotaxin, a secreted lysophospholipase D that produces LPA in biological fluids.

  DOI：

  10.1021/jm049609r
• 作为产物：
  描述：

  11-溴-1-十一醇 在 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.5h， 生成 Δ¹¹-tetradecenol
  参考文献：
  名称：

  Synthesis of insect sex pheromones and their homologues. 2. A convenient method for synthesizing (Z)-alkenols and their acetates.

  摘要：

  通过一种简便的方法，利用Wittig反应将（ω-羟基烷基）三苯基膦盐与烷基醛反应，合成了（Z）-烯醇及其乙酸酯。通过涂有CHDMS的玻璃毛细管柱进行GC分析，评估产物的几何纯度不小于95%的（Z）构型。

  DOI：

  10.1271/bbb1961.44.257

文献信息

• Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates
  申请人：Bedoukian Robert H.

  公开号：US20100113837A1

  公开（公告）日：2010-05-06

  Compounds of the formula (I) wherein R 2 is a branched or unbranched, saturated or ethylenically mono or di unsaturated aliphatic radical, Z is —CH 2 OH, —CH 2 OAc or —CHO, m is a whole positive integer of one or more, and Ac is an acetyl group are synthesized by a process wherein a 1-alken-3-yl alkylate, is reacted with a halo alkanol Grignard reagent.

  式(I)的化合物中，其中R2为支链或未支链、饱和或含有乙烯单元或二元不饱和的脂肪基，Z为—CH2OH、—CH2OAc或—CHO，m为一个或多个正整数，Ac为乙酰基，通过以下过程合成：1-烯丙基烷基化合物与卤代烷醇格氏试剂反应。
• Synthesis of (Z/E)-11-tetradecen-1-ol, a component of Ostrinia nubilalis sex pheromone
  作者：J.-M. Li、J.-P. Yong、H. A. Aisa

  DOI：10.1007/s10600-008-9020-4

  日期：2008.3

  11-Tetradecen-1-ol acetate is a mixture of geometric isomers with the Z/E-conformations in a 94:6 ratio that is used as an attractant to trap corn pests. It has a powerful attractive action similar to that of an isomeric mixture of 11-tetradecenyl acetate with the Z/E-conformation in a 95:5 ratio that was extracted from the peritoneal cavity of male Ostrinia nubilalis Hubner in Xinjing (PRC).

  11-Tetradecen-1-ol acetate 是一种几何异构体混合物，其 Z/E 构型的比例为 94:6，可用作诱捕玉米害虫的引诱剂。它具有强大的诱虫作用，与从中国南京的雄性 Ostrinia nubilalis Hubner 腹腔中提取的 Z/E 构型比例为 95:5 的 11-十四烯基乙酸酯异构体混合物的诱虫作用相似。
• Anti Gram-Positive Bacteria Activity of Synthetic Quaternary Ammonium Lipid and Its Precursor Phosphonium Salt
  作者：Francesca Bacchetti、Anna Maria Schito、Marco Milanese、Sara Castellaro、Silvana Alfei

  DOI：10.3390/ijms25052761

  日期：——

  designing a synthetic path where 1 would be an intermediate to achieve 6. All synthesized compounds were characterized by Fourier-transform infrared spectroscopy and Nuclear Magnetic Resonance. Additionally, potentiometric titrations of NH3+ groups 1 and 6 were performed to further confirm their structure by determining their experimental molecular weight. The antibacterial activities of 1 and 6 were

  有机铵盐和磷盐通过与细菌膜发生致命的相互作用而发挥优异的抗菌作用。特别是，季铵脂质已证明作为基因载体和抗菌剂的有效性。在这里，为了寻找属于这两类的新抗菌装置，我们通过设计合成路径来制备水溶性季铵脂质 (6) 和鏻盐 (1)，其中 1 是实现 6 的中间体。所有合成的化合物通过傅里叶变换红外光谱和核磁共振对其进行了表征。此外，对 NH3+ 基团 1 和 6 进行电位滴定，通过测定其实验分子量来进一步确认其结构。首先针对一系列革兰氏阳性和革兰氏阴性菌种的多重耐药临床分离株评估了1和6的抗菌活性，观察到这两种化合物对肠球菌属和葡萄球菌属的革兰氏阳性分离株具有显着的抗菌活性。对这些物种的更广泛菌株的进一步研究证实了 1 和 6 的显着抗菌作用（MIC 分别为 4-16 和 4-64 µg/mL），而 1 进行的 24 小时杀菌实验不同的金黄色葡萄球菌分离株表现出抑菌行为。此外，化合物1和6在较低的
• A new synthesis of (Z,E)-tetradec-11-enyl acetate, the sex attractant of the omnivorous leafroller (Archips podana)
  作者：V. I. Bykov、L. V. Kelbakiani、T. A. Butenko、E. Sh. Finkel'shtein

  DOI：10.1007/bf01457802

  日期：1996.8

  A four-step synthesis of the title pheromone was elaborated starting from accessible (Z)-cyclooctene and but-1-ene.
• Synthesis of insect sex pheromones and their homologues. 2. A convenient method for synthesizing (Z)-alkenols and their acetates.
  作者：Michio HORIIKE、Masaru TANOUCHI、Chisato HIRANO

  DOI：10.1271/bbb1961.44.257

  日期：——

  (Z)-Alkenols and Their acetates have been synthesized by the Wittig reaction of (ω-hydroxyalkyl)triphenylphosphonium salts with alkanals by a convenient procedure. The geometrical purity of the products was evaluated to be no less than 95% of the (Z)-configu-ration by means of GLC with a glass capillary column coated with CHDMS.

  通过一种简便的方法，利用Wittig反应将（ω-羟基烷基）三苯基膦盐与烷基醛反应，合成了（Z）-烯醇及其乙酸酯。通过涂有CHDMS的玻璃毛细管柱进行GC分析，评估产物的几何纯度不小于95%的（Z）构型。