1,2-difluoro-2-phenylpropane | 59888-14-1

• 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: 1,2-difluoro-2-phenylpropane
• 英文别名: 1,2-Difluor-2-phenylpropann；(1,2-Difluoropropan-2-yl)benzene；1,2-difluoropropan-2-ylbenzene
• CAS: 59888-14-1
• 化学式: C₉H₁₀F₂
• 分子量: 156.175
• InChiKey: CDNXZVNUJRSTMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-苯基-1-丙烯 在 氟化氢吡啶 、 Selectfluor 作用下， 以 乙腈 为溶剂， 以66%的产率得到1,2-difluoro-2-phenylpropane
  参考文献：
  名称：

  Site-selective fluorination of organic compounds using 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts (selectfluor reagents)

  摘要：

  The new ''N-F''-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts8d (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclo[2.2.2]octane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates. These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing alpha-H atoms, certain carbanions, and mildly activated aromatic compounds. The products were obtained with good yields and regioselectivity under very mild reaction conditions.

  DOI：

  10.1021/jo00062a023

文献信息

• Fluorination with XeF2. Part 40. The Important Role of .pi.-Bond Disruption in Fluorine Addition to Phenyl-Substituted Alkenes
  作者：Stojan Stavber、Tjasa Sotler、Marko Zupan、Arkadij Popovic

  DOI：10.1021/jo00099a015

  日期：1994.10

  Ionization potentials (IP) for 11 mono- and alpha,alpha-diphenyl-substituted acyclic and cyclic alkenes 1-11 were measured under the same conditions, using a mass spectrometric technique and applying electron impact ionization. The values, ranging from 8.68 eV for styrene (1) to as low as 7.67 eV for 1,2-dihydro-4-phenylnaphthalene (10), were correlated with the logarithms of the relative rates (k(rel), relative to 1,1-diphenylethene) of fluorine addition across the carbon-carbon double bond in HF-catalyzed reaction of the alkenes with XeF2 in CH2Cl2 at room temperature. The linear relationship between log k(rel) and IP with a regression slope of -2.08 and a correlation constant of 0.942, presented for the first time for any fluorination reaction of organic compounds, demonstrates that ct-bond disruption is the rate-determining step in the fluorine addition process for the series of alkenes 1-11. The course of reaction of the series of three 1-phenyl-benzocyclenes (10-12) with XeF2 was investigated. The addition-elimination process, forming 3-phenyl-2-fluoro-1H-indene (15a), was found exclusively in the case of 9-phenyl-1H-indene (12), while the formation of diastereoisomeric pairs of vicinal difluorides (13 and 14), with the trans isomers slightly predominant, was established in the case of 1,2-dihydro-4-phenylnaphthalene (10) and 6,7-dihydro-9-phenyl-5H-benzocycloheptene (11). On heating the vicinal difluorides 13 and 14 HF was released, thus yielding 3-fluoro-4-phenyl-1,2-dihydronaphthalene (15b) and 6,7-dihydro-8-fluoro-9-phenyl-5H-benzocycloheptene (15c), respectively.
• Fluorination with xenon difluoride. Reaction with phenylsubstituted olefins
  作者：Marko Zupan、Alfred Pollak

  DOI：10.1021/jo00887a015

  日期：1976.12