1-fluoro-4-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctylamino)anthraquinone | 953393-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-fluoro-4-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctylamino)anthraquinone
• 英文别名: 1-Fluoro-4-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctylamino)anthracene-9,10-dione；1-fluoro-4-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctylamino)anthracene-9,10-dione
• CAS: 953393-44-7
• 化学式: C₂₂H₉F₁₆NO₂
• 分子量: 623.293
• InChiKey: FERPHGDMNMVEBM-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  475.6±45.0 °C(Predicted)
• 密度：
  1.638±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  1H,1H-全氟辛基胺 、 1,4-二氟蒽醌 以 二甲基亚砜 为溶剂， 反应 144.0h， 以46%的产率得到1-fluoro-4-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctylamino)anthraquinone
  参考文献：
  名称：

  Synthesis and solid state structure of fluorous probe molecules for fluorous separation applications

  摘要：

  A series of colored hydrocarbon and fluorocarbon tagged 1-fluoro-4-alkylammo-anthraquinones and 1,4-bis-alkylamino-anthraquinone probe molecules were synthesized from a (fluorinated) alkyl amine and 1,4-difluoroanthraquinone to aid in the development of fluorous separation applications The anthraquinones displayed stacking of the anthraquinone tricycle and interdigitation of the (fluorinated) alkyl chains in the solid state Further more, intramolecular N-H O hydrogen bonds forced the hydrocarbon and fluorocarbon tags into a conformation pointing away from the anthraquinone tricycle. with the angle of the tricycle plane normal and the main (fluorinated) alkyl vector ranging from 1 degrees to 39 degrees Separation of the probe molecules on fluorous silica gel showed that the degree of fluorination of the probe molecules plays only a minor role with most eluents (e g, hexane/ethyl acetate and methyl nonafluorobutyl ethers/ethyl acetate) However, toluene as eluent caused a pronounced separation by degree of fluorination for fluorocarbon, but not hydrocarbon tagged probe molecules on both silica gel and fluorous silica gel These studies suggest that hydrocarbon and fluor carbon tagged anthraquinones ate useful probe molecules for the development of laboratory scale fluorous separation applications (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.02.018

文献信息

• Synthesis and solid state structure of fluorous probe molecules for fluorous separation applications
  作者：H.-J. Lehmler、S. Telu、S.M. Vyas、N.S. Shaikh、S.E. Rankin、B.L. Knutson、S. Parkin

  DOI：10.1016/j.tet.2010.02.018

  日期：2010.4

  A series of colored hydrocarbon and fluorocarbon tagged 1-fluoro-4-alkylammo-anthraquinones and 1,4-bis-alkylamino-anthraquinone probe molecules were synthesized from a (fluorinated) alkyl amine and 1,4-difluoroanthraquinone to aid in the development of fluorous separation applications The anthraquinones displayed stacking of the anthraquinone tricycle and interdigitation of the (fluorinated) alkyl chains in the solid state Further more, intramolecular N-H O hydrogen bonds forced the hydrocarbon and fluorocarbon tags into a conformation pointing away from the anthraquinone tricycle. with the angle of the tricycle plane normal and the main (fluorinated) alkyl vector ranging from 1 degrees to 39 degrees Separation of the probe molecules on fluorous silica gel showed that the degree of fluorination of the probe molecules plays only a minor role with most eluents (e g, hexane/ethyl acetate and methyl nonafluorobutyl ethers/ethyl acetate) However, toluene as eluent caused a pronounced separation by degree of fluorination for fluorocarbon, but not hydrocarbon tagged probe molecules on both silica gel and fluorous silica gel These studies suggest that hydrocarbon and fluor carbon tagged anthraquinones ate useful probe molecules for the development of laboratory scale fluorous separation applications (C) 2010 Elsevier Ltd All rights reserved