2,2,3,3,4,4-hexafluoropentane-1,5-diyl bis(N-phenylcarbamate) | 1610024-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2,3,3,4,4-hexafluoropentane-1,5-diyl bis(N-phenylcarbamate)
• 英文别名: [2,2,3,3,4,4-hexafluoro-5-(phenylcarbamoyloxy)pentyl] N-phenylcarbamate
• CAS: 1610024-07-1
• 化学式: C₁₉H₁₆F₆N₂O₄
• 分子量: 450.337
• InChiKey: ICUOBPUWLMQVSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,2,3,3,4,4-六氟环-1,5-戊二醇 、 异氰酸苯酯 以 乙腈 为溶剂， 反应 4.0h， 以63%的产率得到2,2,3,3,4,4-hexafluoropentane-1,5-diyl bis(N-phenylcarbamate)
  参考文献：
  名称：

  Photochemical Activation of Extremely Weak Nucleophiles: Highly Fluorinated Urethanes and Polyurethanes from Polyfluoro Alcohols

  摘要：

  An efficient and environmentally friendly photoreaction between phenyl isocyanate or pentafluorophenyl isocyanate and polyfluorinated alcohols and diols is described for the first time. New highly fluorinated urethanes and diurethanes, derived from aromatic isocyanates, are produced in good yields in a photoreaction that is apparently governed by the acidic properties of the polyfluoro alcohols and diols. The wettability properties of the new polyfluorinated diurethanes have been tested, some of them showing significantly high values of hydrophobicity and oleophobicity. This new photoreaction has also been tested in the production of a model polyfluorinated polyurethane, establishing the influence of the irradiation power in the outcome of the process, and directly achieving a molecular weight distribution corresponding to a number-average DPn = 12 and a highest DPn = 20 after 4 h of irradiation (DPn: "number-average degree of polymerization").

  DOI：

  10.1021/jo5005789

文献信息

• Photochemical Activation of Extremely Weak Nucleophiles: Highly Fluorinated Urethanes and Polyurethanes from Polyfluoro Alcohols
  作者：Marc Soto、Rosa María Sebastián、Jordi Marquet

  DOI：10.1021/jo5005789

  日期：2014.6.6

  An efficient and environmentally friendly photoreaction between phenyl isocyanate or pentafluorophenyl isocyanate and polyfluorinated alcohols and diols is described for the first time. New highly fluorinated urethanes and diurethanes, derived from aromatic isocyanates, are produced in good yields in a photoreaction that is apparently governed by the acidic properties of the polyfluoro alcohols and diols. The wettability properties of the new polyfluorinated diurethanes have been tested, some of them showing significantly high values of hydrophobicity and oleophobicity. This new photoreaction has also been tested in the production of a model polyfluorinated polyurethane, establishing the influence of the irradiation power in the outcome of the process, and directly achieving a molecular weight distribution corresponding to a number-average DPn = 12 and a highest DPn = 20 after 4 h of irradiation (DPn: "number-average degree of polymerization").