1-azido-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctane | 1334419-37-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-azido-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctane
• 英文别名: 8-azido-1,1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluorooctane
• CAS: 1334419-37-2
• 化学式: C₈H₂F₁₅N₃
• 分子量: 425.1
• InChiKey: UVOWRLHHQCIYPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.76
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-azido-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctane 在 copper(ll) sulfate pentahydrate 、 一水合肼 、 sodium ascorbate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 32.0h， 生成 4-aminomethyl-1-((perfluoroheptyl)methyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Fluorous 1,2,3-Triazol-4-ylmethyl Amines and Amine Derivatives for Novel Surfactant Applications

  摘要：

  通过在表面活性剂分子的氨基氮原子上连接取代基，产生了一系列具有附加功能的氟表面活性剂。通过 N-烷基化和 N-酰基化策略合成了含有一个和两个三唑环系统的分子。

  DOI：

  10.1071/ch14458
• 作为产物：
  描述：

  2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl methanesulfonate 在 sodium azide 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 4.5h， 以64%的产率得到1-azido-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctane
  参考文献：
  名称：

  10.3998/ark.5550190.p009.771

  摘要：

  DOI：

  10.3998/ark.5550190.p009.771

文献信息

• Convenient synthesis of pure fluorous alkyl azides at multigram scale
  作者：Máté Berta、András Dancsó、Anikó Nemes、Zoltán Pathó、Dénes Szabó、József Rábai

  DOI：10.1016/j.jfluchem.2016.08.005

  日期：2017.4

  [Rfn(CH2)mX (X = Br, I, OTs, OTf)], and a slight excess of NaN3 in DMSO at 100 °C for 5 h, followed by steam distillation, allowed the isolation of azides Rfn(CH2)mN3 in good to excellent yields with high purity (GC assay ≥98%). Due to the stability of these fluorous azides they can be distilled at atmospheric or lower pressures for further purification. 4-Azidoperfluorotoluene (p-CF3C6F4N3) and 1-azidooctane

  F-烷基化试剂的反应，包括（全氟烷基）烷基卤化物和磺酸盐[R fn（CH 2）m X（X = Br，I，OTs，OTf）]，以及在100°C DMSO中略有过量的NaN 3保持5小时，然后进行水蒸气蒸馏，以高纯度（GC测定≥98％）高至极好产率分离出叠氮化物R fn（CH 2）m N 3。由于这些氟叠氮化物的稳定性，它们可以在大气压或更低的压力下蒸馏以进一步纯化。4-叠氮全氟甲苯（p- CF 3 C 6 F 4 N 3）和1-叠氮辛烷也分别在相似的条件下从全氟甲苯（CF 3 C 6 F 5）或1-碘辛烷开始制备。蒸汽蒸馏可以轻松安全地分离出高达50 g的产品。
• 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。
• 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.