[2,2,3,3,4,4,5,5-Octafluoro-6-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]hexyl] trifluoromethanesulfonate | 1312809-34-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [2,2,3,3,4,4,5,5-Octafluoro-6-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]hexyl] trifluoromethanesulfonate
• 英文别名: [2,2,3,3,4,4,5,5-octafluoro-6-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]hexyl] trifluoromethanesulfonate
• CAS: 1312809-34-9
• 化学式: C₁₆H₂₃F₁₁O₈S
• 分子量: 584.402
• InChiKey: BPSCGTOPNCQXOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [2,2,3,3,4,4,5,5-Octafluoro-6-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]hexyl] trifluoromethanesulfonate 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 273.5h， 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
• 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 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 28.5h， 生成 [2,2,3,3,4,4,5,5-Octafluoro-6-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]hexyl] trifluoromethanesulfonate
  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

• ULTRASOUND-ACTIVATED NANOPARTICLES AS IMAGING AGENTS AND DRUG DELIVERY VEHICLES
  申请人：Chang Andy Y.

  公开号：US20120277573A1

  公开（公告）日：2012-11-01

  The invention provides nanoparticles for delivery of imaging agents, drugs, and other molecules, such as genetic material. The nanoparticles have a core structure comprising the imaging agent and/or drug, and a shell structure that allows for water solubility. The shell structure further provides a barrier with limited water permeability that protects the core. The nanoparticles can be induced to release their cargo by treatment with ultrasound. Methods of delivering drugs and imaging agents are also provided, whereby the nanoparticles are delivered to tissues of interest in a substantially inert form, then activated using ultra-sound to release the drugs or imaging agents.

  这项发明提供了用于传递成像剂、药物和其他分子（如基因物质）的纳米颗粒。这些纳米颗粒具有核心结构，包括成像剂和/或药物，以及允许水溶性的外壳结构。外壳结构进一步提供了一个有限水渗透性的屏障，保护核心。可以通过超声治疗诱导纳米颗粒释放其载荷。还提供了传递药物和成像剂的方法，其中纳米颗粒以基本惰性的形式传递到感兴趣的组织中，然后使用超声激活以释放药物或成像剂。
• 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.
• US9273184B1
  申请人：——

  公开号：US9273184B1

  公开（公告）日：2016-03-01
• [EN] ULTRASOUND-ACTIVATED NANOPARTICLES AS IMAGING AGENTS AND DRUG DELIVERY VEHICLES<br/>[FR] NANOPARTICULES ACTIVÉES PAR ULTRASONS EN TANT QU'AGENTS D'IMAGERIE ET VÉHICULES D'ADMINISTRATION DE MÉDICAMENTS
  申请人：LOS ANGELES CHILDRENS HOSPITAL

  公开号：WO2011079317A2

  公开（公告）日：2011-06-30

  The invention provides nanoparticles for delivery of imaging agents, drugs, and other molecules, such as genetic material. The nanoparticles have a core structure comprising the imaging agent and/or drug, and a shell structure that allows for water solubility. The shell structure further provides a barrier with limited water permeability that protects the core. The nanoparticles can be induced to release their cargo by treatment with ultrasound. Methods of delivering drugs and imaging agents are also provided, whereby the nanoparticles are delivered to tissues of interest in a substantially inert form, then activated using ultrasound to release the drugs or imaging agents.
• Synthesis and phosphonate binding of guanidine-functionalized fluorinated amphiphiles
  作者：Xinping Wu、Emine Boz、Amy M. Sirkis、Andy Y. Chang、Travis J. Williams

  DOI：10.1016/j.jfluchem.2011.12.011

  日期：2012.3

  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.