6-<(tetrahydropyranyl)oxy>hexanoic acid | 32437-88-0

• 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: 6-<(tetrahydropyranyl)oxy>hexanoic acid
• 英文别名: 6-(tetrahydropyran-2-yloxy)hexanoic acid；6-(tetrahydro-2H-pyran-2-yloxy)hexanoic acid；6-(Oxan-2-yloxy)hexanoic acid
• CAS: 32437-88-0
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: ZITIQCQEVOLWQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  360.3±37.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-<(tetrahydropyranyl)oxy>hexanoic acid 在 copper(l) iodide 、 四(三苯基膦)钯 、 三氟甲磺酸三甲基硅酯 、 1-羟基苯并三唑 、 对甲苯磺酸 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 91.0h， 生成
  参考文献：
  名称：

  Mechanism of Ion Transport by Fluorescent Oligoester Channels

  摘要：

  The synthesis and membrane activity of a suite of linear oligoesters containing a common diphenylacetylene unit core and differing in the hydroxyl terminus are reported. Active compounds formed high-conductance channels efficiently in both vesicle and planar bilayers, with one compound showing a very unusual slow loss of transport activity over a 20-30 min period. Steady-state and time-resolved fluorescence studies establish the rapid partition of active compounds to the bilayer and identify at least three types of membrane-associated species by their differing fluorescence lifetimes. The change in the distribution of species is correlated with the slow loss of activity. The results are interpreted in terms of an aggregate within a single bilayer leaflet that is nonetheless competent to transport ionic species through the bilayer. The properties of such structures, revealed by these compounds, appear to be consistent with commonly observed behaviors of other synthetic ion channels.

  DOI：

  10.1021/ja306596m
• 作为产物：
  描述：

  6-(tetrahydro-2H-pyranyloxy)hexan-1-ol 在 potassium bromide 4-(polystyrylMeO)-2,2,6,6-tetraMepiperidin-1-yloxy radical 、 PS-CH₂Me₃(+)*ClO₂(-) 、 PS-CH₂NMe₃(+)*H₂PO₄(-) 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以98%的产率得到6-<(tetrahydropyranyl)oxy>hexanoic acid
  参考文献：
  名称：

  The simultaneous use of immobilised reagents for the one-pot conversion of alcohols to carboxylic acids

  摘要：

  在单个反应容器中同时使用选定的固定氧化试剂，是将伯醇转化为相应羧酸的有效方法。

  DOI：

  10.1039/b201776h

文献信息

• Solid-phase synthesis of a library of linear oligoester ion-channels
  作者：Thomas Murray Fyles、Horace Luong

  DOI：10.1039/b816648j

  日期：——

  A solid-phase synthesis protocol was used to prepare fifteen new linear tetra-, and penta-esters structurally related to an active lead compound. The structures were assembled from three types of hydroxyl protected building blocks: monoalkyl esters of hydroxyglutaric acid, ω-hydroxyacids, and α-hydroxymethylalkanoic acids. The standard methodology gave acceptable quantities of material free of small molecule impurities. Mass spectrometric analysis revealed the presence of deletions due to incomplete coupling, as well as additions and macrolactones due to partial acidic rearrangement on release from the solid-support. The amount of these impurities could be estimated from the 1H NMR spectra, and their implications for subsequent activity analysis are discussed.

  采用固相合成协议制备了十五种新的线性四酯和五酯，这些化合物的结构与一种活性先导化合物相关。结构由三种类型的羟基保护构建块组装而成：羟基戊二酸的单烷基酯、ω-羟基酸和α-羟基甲基烷酸。标准方法得到了数量可接受、未含小分子杂质的材料。质谱分析揭示了因耦合不完全而导致的缺失，以及因从固体支持释放后的部分酸重排而引起的附加物和大环内酯的存在。通过1H NMR光谱可以估计这些杂质的数量，并讨论它们对后续活性分析的影响。
• Species selective diazirine positioning in tag-free photoactive quorum sensing probes
  作者：Luba Dubinsky、Antonia Delago、Neri Amara、Pnina Krief、Josep Rayo、Tsaffrir Zor、Vladimir V. Kravchenko、Michael M. Meijler

  DOI：10.1039/c3cc43092h

  日期：——

  The synthesis and comparison of activities of ‘tag-free’ probes with diazirines at various positions are described. Remarkable differences in their effects on P. aeruginosa and on human bronchial epithelial cells were observed, supporting the efforts to isolate and identify receptors for N-acyl homoserine lactones.

  描述了不同位置的“无标记”探针与二氮环的合成及其活性比较。观察到它们对铜绿假单胞菌和人支气管上皮细胞的影响存在显著差异，这支持了分离和识别N-酰基同源氨基酸内酯受体的研究工作。
• Synthesis, transport activity, membrane localization, and dynamics of oligoester ion channels containing diphenylacetylene units
  作者：Joanne M. Moszynski、Thomas M. Fyles

  DOI：10.1039/c0ob00194e

  日期：——

  Four new linear oligoesters containing a diphenylacetylene unit were prepared by fragment coupling sequences and the ion channel forming ability of the compounds was investigated. Activity in vesicles was very strongly controlled by overall length; the longest compound was effectively inactive. Planar bilayer studies established that all compounds are able to form channels, but that regular step changes in conductance depend on the location of the diphenylacetylene unit within the oligoester and on the electrolyte. The intrinsic fluorescence of the diphenylacetylene unit was used to probe aggregation and membrane localization. Both monomer (320 nm) and excimer (380 nm) emissions are quenched by copper ions; quenching of the excimer emission from an aqueous aggregate is very efficient. Time-dependent changes in the intensities of monomer and excimer emission show slow transfer of diphenylacetylene units from an aqueous aggregate to a membrane-bound monomer with subsequent growth of emission from a membrane-bound excimer. The latter species is not quenched by aqueous copper ions. The implications of these species and processes for the mechanism of ion channel formation by simple oligoesters are discussed.

  制备了四种新型线性寡聚酯，其中包含二苯乙炔单元，并研究了这些化合物的离子通道形成能力。囊泡中的活性受到整体长度的强烈影响；最长的化合物几乎是非活性的。平面双层研究表明，所有化合物都能够形成通道，但导电性发生规律性阶跃变化取决于二苯乙炔单元在寡聚酯中的位置以及电解质的影响。利用二苯乙炔单元的内在荧光来探测聚集和膜定位。单体（320nm）和激基（380nm）发射均被铜离子猝灭；来自水相聚集体的激基发射被猝灭的效果非常显著。单体和激基发射强度的时间依赖变化表明，二苯乙炔单元从水相聚合物缓慢转移到膜结合的单体中，随后膜结合的激基发射逐渐增强。后者物种不受水相铜离子的猝灭。这些物种和过程对简单寡聚酯形成离子通道机制的影响进行了讨论。
• Synthesis and biological evaluation of two glycerolipidic prodrugs of didanosine for direct lymphatic delivery against HIV
  作者：Muriel Lalanne、Angelo Paci、Karine Andrieux、Nathalie Dereuddre-Bosquet、Pascal Clayette、Alain Deroussent、Micheline Ré、Gilles Vassal、Patrick Couvreur、Didier Desmaële

  DOI：10.1016/j.bmcl.2007.01.062

  日期：2007.4

  dipalmitoylphosphatidylcholine was elaborated. A simple quantitative HPLC-UV method was developed and validated, and ESI-MS was used for qualitative purpose. These two prodrugs exhibited promising biological activities against HIV-1 in in vitro infected cell culture.

  合成了设计用于绕过肝脏首过代谢的新的去氧肌苷和去氧肌苷甘油新脂前体药物，并测试了它们的细胞毒性和抗HIV-1活性。精心配制了二棕榈酰磷脂酰胆碱的脂质体制剂。开发并验证了一种简单的定量HPLC-UV方法，并使用ESI-MS进行定性分析。在体外感染的细胞培养中，这两种前药显示出有希望的针对HIV-1的生物学活性。
• Solid-Supported Reagents for the Oxidation of Aldehydes to Carboxylic Acids
  作者：Toshiyasu Takemoto、Kosuke Yasuda、Steven V. Ley

  DOI：10.1055/s-2001-17448

  日期：——

  Solid-supported reagents such as phosphate-buffered (PB) silica gel (SiO2) supported potassium permanganate (KMnO4) and polymer-supported (PS) chlorite have been prepared and used in the conversion of aldehydes to carboxylic acids, affording products without any need for conventional work-up procedures.

  已制备出磷酸盐缓冲（PB）硅胶（SiO2）支撑高锰酸钾（KMnO4）和聚合物支撑（PS）亚氯酸盐等固体支撑试剂，并将其用于醛类到羧酸的转化，无需传统的加工程序即可得到产品。