1,1,1,3,3,3-hexafluoropropan-2-yl N-phenylcarbamate | 1483-40-5

• 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: 1,1,1,3,3,3-hexafluoropropan-2-yl N-phenylcarbamate
• 英文别名: 1,1,1,3,3,3-hexafluoropropan-2-yl phenylcarbamate；Phenylcarbamidsaeure-hexafluorisopropylester；2,2,2-Trifluoro-1-trifluoromethylethyl phenylcarbamate
• CAS: 1483-40-5
• 化学式: C₁₀H₇F₆NO₂
• 分子量: 287.161
• InChiKey: ALMJZSGYPIWRIE-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  190.5±40.0 °C(Predicted)
• 密度：
  1.472±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  六氟异丙醇 、 异氰酸苯酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以80%的产率得到1,1,1,3,3,3-hexafluoropropan-2-yl 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

• <i>Endo</i>-Selective Intramolecular Alkyne Hydroamidation Enabled by NiH Catalysis Incorporating Alkenylnickel Isomerization
  作者：Hoonchul Choi、Xiang Lyu、Dongwook Kim、Sangwon Seo、Sukbok Chang

  DOI：10.1021/jacs.2c03777

  日期：2022.6.8

  Intramolecular alkyne hydroamidation represents a straightforward approach for the access to synthetically valuable cyclic enamides. Despite some advances made in this realm, the ability to attain a precise regiocontrol still remains challenging, especially for endo cyclization that leads to six-membered and larger azacyclic rings. Herein, we report a NiH-catalyzed intramolecular hydroamidation of

  分子内炔烃加氢酰胺化代表了一种获得合成有价值的环状烯酰胺的直接方法。尽管在这一领域取得了一些进展，但获得精确区域控制的能力仍然具有挑战性，特别是对于导致六元和更大氮杂环的内环化。在此，我们报道了一种 NiH 催化的炔基二恶唑酮的分子内加氢酰胺化反应，该反应具有出色的内环选择性，从而提供了范围广泛的六至八元环内烯酰胺。机理研究表明，Ni(I) 催化在当前系统中是有效的，通过区域选择性顺式氢化镍、烯基镍E / Z进行异构化和以 Ni 为中心的内球 Nirenoid 转移。特别是，发现以前缺乏机械理解的关键烯基镍异构化步骤是通过 η 2 -乙烯基过渡态发生的。该协议的合成价值通过将获得的内环烯酰胺非对映选择性修饰为高度功能化的 δ-内酰胺支架来证明。
• Activation of weak nucleophiles: polyfluorocarbamates from polyfluoroalcohols via a fast radical reaction
  作者：Marc Soto、Helena Comalrena、Ursula Balduzzi、Gonzalo Guirado、Vega Lloveras、José Vidal-Gancedo、Rosa María Sebastián、Jordi Marquet

  DOI：10.1016/j.tetlet.2013.09.037

  日期：2013.11

  A new fast radical mechanism has been observed for the reaction of polyfluorinated alcohols and phenylisocyanate, very sensitive to the change of solvents and the concentration of reactants. The acidity of polyfluoroalcohols seems to be responsible for the observed new reactivity and evidences from kinetic studies, electron paramagnetic resonance, cyclic voltammetry, and photostimulation suggest that polyfluoroalkoxy radical is the key intermediate in the chain. To the best of our knowledge, it is the first time that a radical mechanism is described for the preparation of carbamates. (C) 2013 Elsevier Ltd. All rights reserved.
• 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").