trans-2,3,4,5,6-pentafluorophenylazo-4'-methoxybenzene | 85862-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: trans-2,3,4,5,6-pentafluorophenylazo-4'-methoxybenzene
• 英文别名: (E)-1-(4-methoxyphenyl)-2-(perfluorophenyl)diazene；4'-methoxy-2,3,4,5,6-pentafluoroazobenzene；trans 4-(pentafluorophenylazo)anisole；4-methoxyphenylazopentafluorobenzene
• CAS: 85862-23-3
• 化学式: C₁₃H₇F₅N₂O
• 分子量: 302.203
• InChiKey: DFJJALOXSOHDHF-FMQUCBEESA-N

物化性质

• 沸点：
  370.7±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.95
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trans-2,3,4,5,6-pentafluorophenylazo-4'-methoxybenzene 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 nitrosonium tetrafluoroborate 、 三甲基乙酸 作用下， 以 硝基苯 为溶剂， 反应 24.0h， 以55%的产率得到6-methoxy-2-(perfluorophenyl)-2H-benzo[d][1,2,3]triazole 1-oxide
  参考文献：
  名称：

  Rhodium(III)-catalyzed regioselective C H nitrosation/annulation of unsymmetrical azobenzenes to synthesize benzotriazole N-oxides via a RhIII/RhIII redox-neutral pathway

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153049
• 作为产物：
  描述：

  (4-methoxyphenyl)-(2,3,4,5,6-pentafluorophenyl)diazene 以 四氯化碳 为溶剂， 生成 trans-2,3,4,5,6-pentafluorophenylazo-4'-methoxybenzene
  参考文献：
  名称：

  Preparation and photochemical behaviour of 2,3,4,5,6-pentafluorophenylazo-benzene and - 4′-metoxybenzene

  摘要：

  DOI：

  10.1016/s0022-1139(00)81490-6

文献信息

• Synthesis of Azobenzenes from Quinone Acetals and Arylhydrazines
  作者：M. Carmen Carreño、Gerardo Fernández Mudarra、Estíbaliz Merino、María Ribagorda

  DOI：10.1021/jo0498011

  日期：2004.5.1

  Direct reaction between quinone bisacetals and arylhydrazines gives azobenzenes. The presence of catalytic amounts of cerium ammonium nitrate strongly accelerates the reaction. When the bisacetal has a substituent at the 2,5-cyclohexadiene framework, only one regioisomer is formed. The method represents a simple, mild, and novel synthetic access to differently substituted azocompounds in high to excellent

  醌双缩醛与芳基肼之间的直接反应生成偶氮苯。催化量的硝酸铈铵铵的存在强烈地促进了反应。当双缩醛在2，5-环己二烯骨架上具有取代基时，仅形成一种区域异构体。该方法代表了一种简单，温和且新颖的合成方法，可以高收率地获得不同取代的偶氮化合物。
• Electrostatics and Color:  Massive Electrostatic Perturbation of Chromophores by Ion Cluster Ligands
  作者：Robert Weiss、Frank G. Pühlhofer

  DOI：10.1021/ja064907u

  日期：2007.1.1

  The SASAPOS protocol, a general reaction sequence allowing complete exchange of various neutral ligands X in organic, elementorganic, and inorganic systems by cationic ligands L+, has been applied to a variety of pentafluorophenyl-substituted dyes of the general formula C6F5-XY-D (X, Y = N, CH; D = donor substituted arene), yielding the corresponding polycationically substituted dyes. The perturbation of the chromophores by the massive electrostatic effects introduced via the SASAPOS method led to bathochromic shifts of the absorption maxima of up 140 nm, 7600 cm(-1), respectively. A strong dependency of the specific shifts on the nature of the connecting pi linker -XY- (N vs CH) has been detected by UV-vis absorption spectroscopy. Additionally, the effects of resubstitution of cationic ligands L+ by OH and O- have been studied.
• Diazotization of pentafluoroaniline by means of anion-catalyzed phase transfer catalysis in a hydrophobic organic solvent
  作者：Hidetoshi Iwamoto、Takaaki Sonoda、Hiroshi Kobayashi

  DOI：10.1016/s0022-1139(00)83174-7

  日期：1984.4