1-(16,16,17,17,18,18,19,19-octafluoro-2,5,8,11,14-pentaoxaicosan-20-yl)guanidine 2,2,2-trifluoroacetate | 1362739-59-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(16,16,17,17,18,18,19,19-octafluoro-2,5,8,11,14-pentaoxaicosan-20-yl)guanidine 2,2,2-trifluoroacetate
• CAS: 1362739-59-0
• 化学式: C₂HF₃O₂*C₁₆H₂₇F₈N₃O₅
• 分子量: 607.419
• InChiKey: AVKKASXNMNTXIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  39.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  145.35
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2,5,8,11-四氧杂十三烷-13-基4-甲基苯磺酸酯 在 sodium hydride 、 三乙胺 、 N,N-二异丙基乙胺 、 肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 292.5h， 生成 1-(16,16,17,17,18,18,19,19-octafluoro-2,5,8,11,14-pentaoxaicosan-20-yl)guanidine 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Synthesis and phosphonate binding of guanidine-functionalized fluorinated amphiphiles

  摘要：

  We report herein convenient procedures for the use of highly fluorinated alpha,omega-diols (e.g. 1) as building blocks for the rapid assembly of amphiphilic materials containing a fluorous phase region. We describe expedient conversion of the parent diols to both symmetrically and asymmetrically substituted amphiphiles via the installation of an intermediate trifluoromethanesulfonyl ester. These sulfonate esters are versatile and easily manipulated intermediates, which can be readily converted to a variety of nitrogen, halogen, and carbon groups. Moreover, we show that for guanidine-terminated fluorous amphiphiles, these molecules can bind phosphonic acid groups in aqueous media. Thus, these materials offer a new strategy for decorating phosphorylated biomolecules with fluorine-rich coatings. (C) 2012 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2011.12.011

文献信息

• A noncovalent, fluoroalkyl coating monomer for phosphonate-covered nanoparticles
  作者：Vincent Li、Andy Y. Chang、Travis J. Williams

  DOI：10.1016/j.tet.2013.05.092

  日期：2013.9

  Gadolinium-containing phosphonate-coated gold nanoparticles were prepared and then non-covalently coated with an amphiphilic fluorous monomer. The monomer spontaneously self-assembles into a noncovalent monolayer shell around the particle. The binding of the shell utilizes a guanidinium phosphonate interaction analogous to the one exploited by the Wender molecular transporter system. Particle shell binding was characterized by a 27% decrease in F-19 T-1 of the fluorous shell upon exposure to the paramagnetic gadolinium in the particle and a corresponding increase in hydrodynamic diameter from 3 nm to 4 nm. Interestingly, a much smaller modulation of F-19 T-1 is observed when the shell monomer is treated with a phosphonate-free particle. By contrast, the phosphonate-free particle is a much more relaxive H-1 T-1 agent for water. Together, these observations show that the fluoroalkylguanidinium shell binds selectively to the phosphonate-covered particle. The system's relaxivity and selectivity give it potential for use in F-19 based nanotheranostic agents. (C) 2013 Elsevier Ltd. All rights reserved.