1,6-difluorodibenzodioxin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶英
• 英文名称: 1,6-difluorodibenzodioxin
• 英文别名: 1,6-Difluoro DBD；1,6-difluorodibenzo-p-dioxin
• 化学式: C₁₂H₆F₂O₂
• 分子量: 220.175
• InChiKey: SUZZELGAHSENSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,6-二氟苯酚 在 base 作用下， 反应 12.0h， 以5.4%的产率得到1,6-difluorodibenzodioxin
  参考文献：
  名称：

  Synthesis of polyfluorinated dibenzo-p-dioxins

  摘要：

  Fluorinated dibenzo-p-dioxins (PFDD) have been selectively synthesized from fluorophenols and isolated by liquid-column- and thin layer chromatography. The structures were confirmed by IR, MS, HR-MS, H-1-NMR and F-19-NMR-spectroscopy. Reaction times, melting points and the IR-absorption bands are presented for several PFDD's as well as H-1- and (19)-F-NMR-spectra for two PFDD's and the mass-spectrum for 2,3,7,8-T4FDD.

  DOI：

  10.1016/0045-6535(94)90346-8

文献信息

• Polyfluorinated dibenzodioxins and dibenzofurans — synthesis, analysis, formation and toxicology
  作者：R. Weber、D. Schrenk、H.-J. Schmitz、A. Hagenmaier、H. Hagemnaier

  DOI：10.1016/0045-6535(94)00429-x

  日期：1995.2

  The 75 congeners of the polyfluorinated dibenzodioxins (PFDDs) and about half of the 135 polyfluorinated dibenzofurans (PFDFs) have been synthesized by pyrolysis of fluorophenols and fluorobenzenes. The individual congeners were characterized by GC/MS. 2,3,7,8-TFDD was also characterized by H-1-, C-13- and F-19-NMR spectroscopy. The retention behavior of PFDDs and PFDFs during gaschromatographic separation is entirely different from that of PCDDs/PCDFs or PBDDs/PBDFs. The PFDDs/PFDFs elute earlier than the PCDDs/PCDFs and the order of the elution is not governed by the degree of substituion, O8FDD eluting e.g. much earlier than the M(1)FDDs.A preliminary toxicological evaluation of 2,3,7,8-TFDD was carried out. The elimination of 2,3,7,8-TFDD from mice after a single i.p. injection is biphasic with a very rapid elimination half-live of 5 minutes and a slower phase of 165 minutes. This means a dramatically reduced half-live compared to 2,3,7,8-TCDD with 8.5 d. In liver the TFDD level reaches a maximum 30 minutes after injection and also declined in a biphasic manner. In rat hepatocytes a primary culture induction of CYP4501A1-catalyzed EROD activity could be demonstrated, indicating that 2,3,7,8-TFDD activates the dioxin receptor. In rat hepatocyte cultures similar EC(50) values were found for 2,3,7,8-TCDD and 2,3,7,8-TFDD.So far no de novo synthesis of PFDD/PFDF could be detected under conditions were PCDDs/PCDFs are formed Also, formation of PFDDs/PFDFs could not be detected during thermal treatment of fluorotrichloromethane or Teflon.
• Synthesis of polyfluorinated dibenzo-p-dioxins
  作者：U. Haffer、W. Rotard、W. Mailahn

  DOI：10.1016/0045-6535(94)90346-8

  日期：1994.11

  Fluorinated dibenzo-p-dioxins (PFDD) have been selectively synthesized from fluorophenols and isolated by liquid-column- and thin layer chromatography. The structures were confirmed by IR, MS, HR-MS, H-1-NMR and F-19-NMR-spectroscopy. Reaction times, melting points and the IR-absorption bands are presented for several PFDD's as well as H-1- and (19)-F-NMR-spectra for two PFDD's and the mass-spectrum for 2,3,7,8-T4FDD.