4-(((1-n-octyl-1H-1,2,3-triazol-4-yl)methoxy)methyl)-1-(2-(perfluorohexyl)ethyl)-1H-1,2,3-triazole | 1334419-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(((1-n-octyl-1H-1,2,3-triazol-4-yl)methoxy)methyl)-1-(2-(perfluorohexyl)ethyl)-1H-1,2,3-triazole
• 英文别名: 1-Octyl-4-[[1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)triazol-4-yl]methoxymethyl]triazole
• CAS: 1334419-39-4
• 化学式: C₂₂H₂₇F₁₃N₆O
• 分子量: 638.475
• InChiKey: QQLUGSBZZOQCIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  1-azidooctane 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 sodium hydroxide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.25h， 生成 4-(((1-n-octyl-1H-1,2,3-triazol-4-yl)methoxy)methyl)-1-(2-(perfluorohexyl)ethyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Towards functional fluorous surfactants. Synthesis of hydrophilic fluorous 1,2,3-triazolylmethyl ethers and di(1,2,3-triazolylmethyl) ethers

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2011.07.002

文献信息

• Titration characteristics of fluorous 1,2,3-triazol-4-ylmethyl ethers, bis(1,2,3-triazol-4-ylmethyl) ethers and bis(1,2,3-triazol-4-ylmethyl) amines
  作者：Dominic V. Francis、Jason B. Harper、Roger W. Read

  DOI：10.1016/j.jfluchem.2016.10.012

  日期：2016.12

  changes in chemical shift of the H5 triazolyl signals provide consistent information that support weak but evident cooperativity between the triazolyl rings in bis-triazolylmethyl ethers. This is overridden by replacement of the ether oxygen with a secondary amino group, but similar principles apply in subsequent protonation. An attempt is made to interpret the cooperative behavior.

  用1 H NMR光谱法检测了用樟脑磺酸滴定的一系列氟双（1,2,3-三唑-4-基甲基）分子，以研究质子化时可能发生的任何构象变化；设想该信息将有助于预测其作为配体的潜力。基于质子平衡常数和H5三唑基信号化学位移变化的结构活性关系提供了一致的信息，该信息支持双三唑基甲基醚中三唑基环之间的弱但明显的协同作用。这可以通过用仲氨基取代醚氧来取代，但是类似的原理适用于随后的质子化。试图解释合作行为。