cis-1-Phenyl-1,2-difluoro-1,2,3,4-tetrahydronaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: cis-1-Phenyl-1,2-difluoro-1,2,3,4-tetrahydronaphthalene
• 英文别名: (3R,4S)-3,4-difluoro-4-phenyl-2,3-dihydro-1H-naphthalene
• 化学式: C₁₆H₁₄F₂
• 分子量: 244.284
• InChiKey: WIMMITTXZNUYGK-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-1-Phenyl-1,2-difluoro-1,2,3,4-tetrahydronaphthalene 生成 3-Fluoro-4-phenyl-1,2-dihydronaphthalene
  参考文献：
  名称：

  Stavber Stojan, Sotler Tjaa, Zupan Marko, Popovi Arkadij, J. Org. Chem., 59 (1994) N 20, S 5891- 5894

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氢-1-苯基萘 以29%的产率得到
  参考文献：
  名称：

  Stavber Stojan, Sotler Tjaa, Zupan Marko, Popovi Arkadij, J. Org. Chem., 59 (1994) N 20, S 5891- 5894

  摘要：

  DOI：

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.
• Stavber Stojan, Sotler Tjaa, Zupan Marko, Popovi Arkadij, J. Org. Chem., 59 (1994) N 20, S 5891- 5894
  作者：Stavber Stojan, Sotler Tjaa, Zupan Marko, Popovi Arkadij

  DOI：——

  日期：——