4-N,N-diethylamino-4'-bromobiphenyl | 27004-23-5

• 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: 4-N,N-diethylamino-4'-bromobiphenyl
• 英文别名: 4-bromo-4'-(N,N-diethylamino)biphenyl；4-(4-bromophenyl)-N,N-diethylaniline
• CAS: 27004-23-5
• 化学式: C₁₆H₁₈BrN
• 分子量: 304.23
• InChiKey: JFKLNVZUTAMNIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-N,N-diethylamino-4'-bromobiphenyl 、 1-萘基溴化镁, 0.5M IN METHF 以 四氢呋喃 为溶剂， 反应 19.0h， 以22%的产率得到1-(p-(N,N-diethylamino)biphenyl)naphthalene
  参考文献：
  名称：

  Photoinduced Intramolecular Electron Transfer in p-Polyphenylamines and 1-(p-(N,N-Dialkylamino)-p-polyphenyl)naphthalenes

  摘要：

  Photoinduced intramolecular electron transfer in two series of aromatic amines of the type aryl-(C6H4),-NR(2), where aryl is phenyl and l-naphthyl and n = 1-3, has been studied. From the solvatochromic behavior of the fluorescences from these compounds, excited-state dipole moments ranging from 10.9 to 29.9 D have been measured, suggesting that the emissions occur from charge-transfer states, except in 4-(N,N-diethylamino)biphenyl (aryl = phenyl; n = 1). The large quantum yields and short fluorescence lifetimes indicate efficient electronic communication between the donor and acceptor (k(et) > 10(8) s(-1)). Good agreement was found between the observed and calculated fluorescence energies in polar solvents using a simple electrostatic model. The results suggest that the phenyl rings in the extended systems act as part of the donor or acceptor moieties in electron transfer and are not spacer (or insulating) groups.

  DOI：

  10.1021/j100077a002
• 作为产物：
  描述：

  4-溴苯硼酸 、 4-(N,N-diethylamino)benzenediazonium tetrafluoroborate 在 [(1,3-dimesitylimidazol-2-ylidene)(naphthoquinone)Pd⁽⁰⁾]2 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以99%的产率得到4-N,N-diethylamino-4'-bromobiphenyl
  参考文献：
  名称：

  Synthesis of Monocarbenepalladium(0) Complexes and Their Catalytic Behavior in Cross-Coupling Reactions of Aryldiazonium Salts

  摘要：

  The first monocarbenepalladium(0) complexes with benzoquinone and naphthoquinone as additional ligands have been prepared. As demonstrated by NMR spectroscopy and X-ray analysis, the complexes show a unique coordination mode giving quinone-bridged dimers. The monocarbenepalladium(0) complexes allow efficient cross-coupling reactions of aryldiazonium salts with olefins (Heck reaction) and arylboronic acids (Suzuki reaction).

  DOI：

  10.1002/1521-3765(20020902)8:17<3901::aid-chem3901>3.0.co;2-e