1-tetrahydropyranyloxy-7-tetradecyne | 37043-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-tetrahydropyranyloxy-7-tetradecyne
• 英文别名: 2-(7-tetradecynyl-1-oxy)tetrahydropyran；2-(7-Tetradecynyloxy)tetrahydropyran；2-(tetradec-7-yn-1-yloxy)tetrahydro-2H-pyran；2-tetradec-7-ynyloxy-tetrahydro-pyran；2-tetradec-7-ynoxyoxane
• CAS: 37043-40-6
• 化学式: C₁₉H₃₄O₂
• 分子量: 294.478
• InChiKey: IURKZIUZLFYYNZ-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氘代氯仿、二氯甲烷、二甲基亚砜、乙酸乙酯、

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-tetrahydropyranyloxy-7-tetradecyne 在 Lindlar's catalyst 吡啶 、 喹啉 、 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 正戊烷 为溶剂， 反应 3.0h， 生成 顺-7-十四碳乙酸酯
  参考文献：
  名称：

  Rossi, Renzo; Carpita, Adriano; Gaudenzi, Loretta, Gazzetta Chimica Italiana, 1980, vol. 110, # 4, p. 237 - 246

  摘要：

  DOI：
• 作为产物：
  描述：

  6-溴正己醇 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-tetrahydropyranyloxy-7-tetradecyne
  参考文献：
  名称：

  Efficient Synthesis of Unsaturated 1-Monoacyl Glycerols for in meso Crystallization of Membrane Proteins

  摘要：

  建立了高度有效的未饱和1-单酰甘油合成方法，以满足膜蛋白结晶中使用的脂质介晶材料迫切需要。

  DOI：

  10.1055/s-0030-1259912

文献信息

• The molecular structure of thio-ether fatty acids influences PPAR-dependent regulation of lipid metabolism
  作者：Jenny Lund、Camilla Stensrud、Rajender、Pavol Bohov、G. Hege Thoresen、Rolf K. Berge、Michael Wright、Ahmed Kamal、Arild C. Rustan、Andrew D. Miller、Jon Skorve

  DOI：10.1016/j.bmc.2016.01.045

  日期：2016.3

  Thio-ether fatty acids (THEFAs), including the parent 2-(tetradecylthio)acetic acid (TTA), are modified fatty acids (FAs) that have profound effects on lipid metabolism given that they are blocked for β-oxidation, and able to act as peroxisome proliferator-activated receptor (PPAR) agonists. Therefore, TTA in particular has been tested clinically for its therapeutic potential against metabolic syndrome

  硫醚脂肪酸（THEFAs），包括母体2-（十四烷基硫代）乙酸（TTA），是经过修饰的脂肪酸（FAs），对脂类代谢具有深远的影响，因为它们被β-氧化所阻断，并且能够充当过氧化物酶体增殖物激活受体（PPAR）激动剂。因此，特别是已经对TTA进行了针对代谢综合征相关疾病的治疗潜力的临床测试。在这里，我们描述了基于具有双键或三键的TTA支架的THEFAs的制备。它们在培养的人骨骼肌细胞（肌管）中以游离酸的形式或在酯化后以磷脂，溶血磷脂或单酰基甘油的形式进行测试。通过FA底物摄取和氧化研究，根据肌管中细胞的生物利用度评估代谢作用，以及选择的PPAR调控基因的基因调控研究。我们注意到，包含三键会促进THEFA介导的FA氧化。此外，THEFA作为溶血磷脂的酯化也促进了FA的氧化作用。鉴于剂量限制和不良的生物利用度抵消了TTA给药的明显临床益处，我们讨论了选择最新的THEFAs和含THEFA的脂质可能能够
• Synthesis of Carboxymethyl GLA-60 Ether Derivatives Containing an Olefin in Their Chains and Their LPS-Antagonistic Activities
  作者：Tsuyoshi Nakamura、Yukiko Watanabe、Masao Shiozaki、Saori Kanai、Shin-ichi Kurakata

  DOI：10.1246/bcsj.76.1011

  日期：2003.5

  Anomeric carboxymethyl GLA-60 olefine derivatives having ether chains instead of ester chains in their side chains were synthesized and their biological activities toward both human U937 cells and mouse PEC-macrophage cells were measured. The species-specific behavior of these compounds in humans (LPS-antagonistic) and mice (very weak LPS-antagonistic, but almost inactive) found this time was different from that in humans (LPS-antagonistic) and mice (endotoxic) found in the biosynthetic precursor of lipid A, such as lipid IVa. However, this fact also shows, interestingly enough, that a difference exists in the molecular recognition between human and mouse LPS receptors.

  合成了具有醚链而非酯链的异构体羧甲基GLA-60烯烃衍生物，并测定了它们对人类U937细胞和小鼠PEC-巨噬细胞的生物活性。这些化合物在人体（LPS拮抗作用）和小鼠（LPS拮抗作用非常弱，但几乎没有活性）中的物种特异性行为与脂质A的生物合成前体脂质IVa中发现的人类（LPS拮抗作用）和小鼠（内毒性）的行为不同。然而，这一事实有趣地表明，人类和小鼠LPS受体之间存在分子识别的差异。
• Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: substrate precursors for cytochrome P450BioI
  作者：Arti A. Singh、Siti N.A. Zulkifli、Michaela Meyns、Patricia Y. Hayes、James J. De Voss

  DOI：10.1016/j.tetasy.2011.08.027

  日期：2011.10

  A series of highly enantioenriched hydroxy- and dihydroxy-fatty esters were required as part of our ongoing investigation into cytochrome P450(BioI). This mediates the biosynthesis of pimelic acid via C-C bond cleavage of long chain fatty acids within Bacillus subtilis. Herein we report the synthesis of various stereoisomers of methyl 7-hydroxytetradecanoate, methyl 8-hydroxytetradecanoate, and methyl 7,8-dihydroxytetradecanoate in highly enantioenriched form, using a combination of asymmetric synthesis and a preparative enantioselective HPLC is reported. (C) 2011 Elsevier Ltd. All rights reserved.
• ——
  作者：M. Subchev、A. Harizanov、W. Francke、S. Franke、E. Plass、A. Reckziegel、F. Schröder、J. A. Pickett、L. J. Wadhams、C. M. Woodcock

  DOI：10.1023/a:1022438717287

  日期：——

  The sex pheromone of the vine bud moth, Theresimima ampellophaga, released at the 3rd-5th abdominal tergites, was identified by coupled GC-EAG, GC-MS, and synthesis as (2S)-butyl (7Z)-tetradecenoate. For the first time, full stereochemistry is unambiguously defined for the sex pheromone of a member of the Zygaenidae. The synthetic compound caught significant numbers of males in field-trapping experiments.
• Tumor inhibitors. 3. Identification and synthesis of a oncolytic hydrocarbon from American coneflower roots
  作者：Denys J. Voaden、Martin Jacobson

  DOI：10.1021/jm00276a013

  日期：1972.6