3-((2-perfluorohexyl)ethoxy)prop-1-yne | 1334419-24-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((2-perfluorohexyl)ethoxy)prop-1-yne
• 英文别名: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-[(prop-2-yn-1-yl)oxy]octane；1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-prop-2-ynoxyoctane
• CAS: 1334419-24-7
• 化学式: C₁₁H₇F₁₃O
• 分子量: 402.155
• InChiKey: UHVIBVXXGUDLQH-UHFFFAOYSA-N

物化性质

• 沸点：
  125-128 °C(Press: 0.1 Torr)
• 密度：
  1.482±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3-((2-perfluorohexyl)ethoxy)prop-1-yne 在 3% Cu/C 、 水 、 三乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 为溶剂， 反应 16.0h， 生成 tetrabutylphosphonium 4-{[2-(perfluorohexyl)ethoxy]methyl}-1H-1,2,3-triazol-1-ide
  参考文献：
  名称：

  非质子杂环阴离子三唑化物离子液体 - 一种通过惠斯根环加成反应获得的新型离子液体阴离子

  摘要：

  三唑核是一种用途广泛的杂环，可以通过 Cu(I) 催化的 Huisgen 环加成反应轻松获得。在此，我们介绍了包含 1,2,3-三唑阴离子的离子液体的制备。这些离子液体是通过简单的方法制备的，在 1-位使用碱不稳定的新戊酰基甲基，它可以作为 1 H -4-取代的 1,2,3-三唑的前体。这些三唑随后在使用合适的离子液体阳离子氢氧化物去质子化之后转化为离子液体。测量了这些离子液体的密度和热分解。这些新型离子液体在气体分离和无金属催化方面具有潜在的应用价值。

  DOI：

  10.1055/s-0033-1338435
• 作为产物：
  描述：

  3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟-1-辛醇 、 3-溴丙炔 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 、 甲苯 为溶剂， 反应 16.5h， 以38%的产率得到3-((2-perfluorohexyl)ethoxy)prop-1-yne
  参考文献：
  名称：

  含尾部NHC配体的Pd配合物的合成及其在半连续膜辅助Suzuki交叉偶联过程中的应用

  摘要：

  均相催化已被证明是制备多种分子实体的可靠方法，但催化剂价格昂贵且难以去除。因此，工业上的目标是容易分离和回收并且具有增加的周转次数的催化剂。从多功能间歇式反应器向精细化学品合成的连续生产的不断转变导致了对催化剂的新要求。本文报道了适用于基于膜辅助反应器的半连续Suzuki交叉偶联反应的Pd配合物的设计和使用。这些Pd配合物包含尾状N-杂环卡宾（NHC）配体，可通过有机溶剂纳米过滤和顶层改性的陶瓷膜进行内部催化剂回收。这些膜基于尺寸排阻和亲和力分离（溶剂-溶质-膜相互作用）的组合，对催化剂进行选择性的纳滤。通过简单地向反应容器中添加更多的反应物和试剂，开发出的半连续系统可显着提高周转次数，简化产品分离并因此降低质量强度。

  DOI：

  10.1021/acs.oprd.8b00273

文献信息

• Towards Functional Fluorous Surfactants. Synthesis and Spectroscopic Features of Systematically Modified Sugar-Substituted Fluorous 1,2,3-Triazoles
  作者：Ahmed M.A. Ahmed、Adnan I. Mohammed、Roger W. Read

  DOI：10.1016/j.jfluchem.2020.109519

  日期：2020.6

  of homologous compounds making up a total of 30 new, fluorous 1-substituted 1,2,3-triazol-4-ylmethyl(and ethyl) ether surfactant candidates, with highly systematic variations in substituent position and type, have been synthesised in consistently good yields by processes involving copper(I)-accelerated Huisgen-Meldal dipolar cycloaddition reactions. Each series contains a perfluorobutylethyl, perfluorohexylethyl

  由10个系列的同源化合物组成的库，总共有30种新的氟代1-取代的1,2,3-三唑-4-甲基（和乙基）醚表面活性剂候选物，其取代基的位置和类型高度系统地变化通过涉及铜（I）加速的惠斯根-梅德尔偶极环加成反应的过程以始终如一的高收率合成了苯甲酸。每个系列在三唑位置N（1）处或通过三唑醚氧连接的全氟丁基乙基，全氟己基乙基或全氟辛基乙基取代基，以及在另一个三唑位置的1-β-D-葡萄糖基或6-α-D-半乳糖基取代基。一半的文库是直接用保护形式的糖成分（过乙酰化的葡萄糖衍生物和1,2：3， 所有的三唑都是可作为氟表面活性剂进行研究的候选物，它们可以在两亲性伙伴状态之间切换，在保护糖的情况下是疏水的，在未保护糖中是亲水的。作为表面活性剂研究的序幕，检查了新建立的化合物库的NMR光谱特征。参照相关文献类似物，对每个系列之内和之间的数据进行比较和对比。未保护的6-半乳糖基衍生物的分析由于众所周知的半缩醛吡喃
• Glucosamine- and galactosamine- based monosaccharides with highly fluorinated motifs
  作者：Joanna Tomaszewska、Karolina Kowalska、Katarzyna Koroniak-Szejn

  DOI：10.1016/j.jfluchem.2016.09.002

  日期：2016.11

  Synthesis of modified monosaccharides, derivatives of glucose and galactose, having a highly fluorinated chain, as a library of synthetic building blocks for hyaluronic acid (HA) modified subunits has been developed. “Click” chemistry has been employed as a strategy for the synthesis of these molecules. 1,2,3-triazole ring derivatives were obtained with good to excellent yields.

  已经开发了具有高度氟化的链的修饰的单糖，葡萄糖和半乳糖的衍生物的合成，作为透明质酸（HA）修饰的亚基的合成构件库。“点击”化学已被用作合成这些分子的策略。获得1,2,3-三唑环衍生物，具有良好至优异的产率。
• Probing the effect of electron donation on CO2 absorbing 1,2,3-triazolide ionic liquids
  作者：Robert L. Thompson、Wei Shi、Erik Albenze、Victor A. Kusuma、David Hopkinson、Krishnan Damodaran、Anita S. Lee、John R. Kitchin、David R. Luebke、Hunaid Nulwala

  DOI：10.1039/c3ra47097k

  日期：——

  Development of the next generation materials for effective separation of gases is required to address various issues in energy and environmental applications. Ionic liquids (ILs) are among the most promising material types. To overcome the many hurdles in making a new class of materials technologically applicable, it is necessary to identify, access, and scale up a range of representative substances. In this work, CO2 reactive triazolide ILs were synthesized and characterized with the aim of developing a deeper understanding of how structural changes affect the overall properties of these substances. It was found that substituents on the anion play a crucial role in dictating the physical properties for CO2 capture. Depending upon the anion substituent, CO2 capacities between 0.07 and 0.4 mol CO2 per mol IL were observed. It was found that less sterically-hindered anions and anions containing electron donating groups were more reactive towards CO2. Detailed spectroscopic, CO2 absorption, rheological, and simulation studies were carried out to understand the nature and influence of these substituents. The effect of water content was also evaluated, and it was found that water had an unexpected impact on the properties of these materials, resulting in an increased viscosity, but little change in the CO2 reactivity.

  要解决能源和环境应用中的各种问题，就必须开发有效分离气体的下一代材料。离子液体 (IL) 是最有前途的材料类型之一。为了克服在技术上应用一类新材料的诸多障碍，有必要识别、获取和放大一系列具有代表性的物质。在这项研究中，我们合成了二氧化碳活性三唑烷基惰性化合物并对其进行了表征，目的是深入了解结构变化如何影响这些物质的整体特性。研究发现，阴离子上的取代基在决定二氧化碳捕获的物理性质方面起着至关重要的作用。根据阴离子取代基的不同，每摩尔 IL 的二氧化碳捕获能力介于 0.07 至 0.4 摩尔 CO2 之间。研究发现，立体阻碍较少的阴离子和含有电子捐赠基团的阴离子对二氧化碳的反应性更强。为了解这些取代基的性质和影响，进行了详细的光谱、二氧化碳吸收、流变和模拟研究。此外，还评估了水含量的影响，结果发现水对这些材料的性质产生了意想不到的影响，导致粘度增加，但二氧化碳反应性几乎没有变化。
• Towards functional fluorous surfactants. Synthesis of hydrophilic fluorous 1,2,3-triazolylmethyl ethers and di(1,2,3-triazolylmethyl) ethers
  作者：Dominic V. Francis、D. Howard Miles、Adnan I. Mohammed、Roger W. Read、Xiaobei Wang

  DOI：10.1016/j.jfluchem.2011.07.002

  日期：2011.11

  Copper(I)-accelerated Huisgen-Meldal dipolar cycloaddition reactions between polyfluoroalkyl azides and propargyl ethers of n-octanol and of triethyleneglycol monomethyl ether exhibited variation in yield of 1,2,3-triazol-4-ylmethyl ethers. Microwave acceleration, and in situ generation of the azides, provided improvements in yield and efficiency. In contrast, very good yields of equivalent fluorous triazoles were obtained from a range of n-alkyl azides with propargyl ethers of perfluorohexylethanol and of perfluoroheptylmethanol through conventional copper(I)-promoted reactions. Together, the resulting substances with systematic variations in polyfluoroalkyl and alkyl substituent length and position of substitution, and degree of oxygen content, make up small libraries of hybrid fluorous 1,2,3-triazol-4-ylmethyl ethers as candidates for study as hydrophilic fluorous surfactants. In addition, a pilot sample of di(1,2,3-triazol-4-ylmethyl) ethers with 1'-octyl-1-polyfluoroalkyl-substituents and 1'-nonyl-1-perfluorooctylethyl substituents were synthesised for the first time in an effort to develop more functional, fluorous surfactants. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis of Novel Silanes Functionalized with Mono- and Bis-Fluoroalkylated [1,2,3]-Triazoles
  作者：Lu Cai、Yanhua Yuan、Zhanxiong Li、Wanjun Wang

  DOI：10.1080/10426507.2015.1032411

  日期：2015.11.2

  In the current work, a series of mono-fluoroalkylated [1,2,3]-triazole precursors was prepared by the 1,3-dipolar cycloaddition reaction of allyl azide and perfluoroalkylethoxyl propynes, in which the CuSO4 and sodium ascorbate were used as the catalyst. Using these precursors as unsaturated substrates, a series of novel mono-fluoroalkyldichloromethyl silanes were successfully synthesized via hydrosilylation between CC and Si-H bonds. Furthermore, to construct fluorosilanes with two or more stacked fluoroalkyl groups in one molecule, silanes with bis-fluoroalkylated [1,2,3]-triazoles as pendants were synthesized afterwards.