trans-2,3,4,5,6-pentafluoro-4'-dimethylaminostilbene | 368421-21-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-2,3,4,5,6-pentafluoro-4'-dimethylaminostilbene
• 英文别名: (E)-4'-dimethylamino-2,3,4,5,6-pentafluorostilbene；trans-2,3,4,5,6-Pentafluoro-4'-dimethylamino-stilbene；N,N-dimethyl-4-[(E)-2-(2,3,4,5,6-pentafluorophenyl)ethenyl]aniline
• CAS: 368421-21-0
• 化学式: C₁₆H₁₂F₅N
• 分子量: 313.27
• InChiKey: YGZCNCINOKBTSH-VMPITWQZSA-N

物化性质

• 熔点：
  172-173 °C(Solv: ethanol (64-17-5))
• 沸点：
  343.0±42.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-2,3,4,5,6-pentafluoro-4'-dimethylaminostilbene 反应 15.0h， 以100%的产率得到4,4'-((1R,2R,3S,4S)-2,4-bis(perfluorophenyl)cyclobutane-1,3-diyl)bis(N,N-dimethylaniline)
  参考文献：
  名称：

  新型氟化氨基对苯二酚及其固态光二聚化†

  摘要：

  我们通过4-哌嗪基-苯并甲醛与 五氟亚苄基三苯基膦并且我们分析了这些斯蒂尔苯在固态下的光化学行为；多亏了芳烃–全氟芳烃 π–π相互作用，其中一些已经显示出给出相应的良好趋势 环丁烷光二聚体的定量收率。溶液和聚合物基体中的光环化都是可逆的，从而提供具有不同顺式-反式立体选择性的相应的对苯二酚。

  DOI：

  10.1039/c0nj00264j
• 作为产物：
  描述：

  α-溴-2,3,4,5,6-五氟甲基苯酸酯 在 正丁基锂 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.33h， 生成 trans-2,3,4,5,6-pentafluoro-4'-dimethylaminostilbene
  参考文献：
  名称：

  Synthesis and Spectroscopic and NLO Properties of “Push-Pull” Structures Incorporating the Inductive Electron-Withdrawing Pentafluorophenyl Group

  摘要：

  A series of "push-pull" molecules, each incorporating a pentafluorophenyl ring as an inductive accepting group, has been synthesised. The NLO properties of these compounds were measured in solution by EFISH (operating at 1907 nm) and in the solid state by the Kurtz powder technique (at 1907 nm). Values of mubeta, the product of the molecule dipole moment and its first-order hyperpolarizdbility, of up to 200 x 10(-48) esu were obtained.((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200204)2002:8<1380::aid-ejoc1380>3.0.co;2-d

文献信息

• 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.
• Novel fluorinated amino-stilbenes and their solid-state photodimerization
  作者：Antonio Papagni、Paola Del Buttero、Chiara Bertarelli、Luciano Miozzo、Massimo Moret、Mary T. Pryce、Silvia Rizzato

  DOI：10.1039/c0nj00264j

  日期：——

  We synthesized a series of polyfluoro-amino-stilbenes in satisfactory yields by Wittig reaction of 4-piperazinyl-benzalhehydes with pentafluoro-benzylidene-triphenyl-phosphorane and we analyzed the photochemical behavior of these stilbenes in the solid state; thanks to arene–perfluoroarene π–π interactions, some of them have shown a good propensity to give the corresponding cyclobutane photodimers

  我们通过4-哌嗪基-苯并甲醛与 五氟亚苄基三苯基膦并且我们分析了这些斯蒂尔苯在固态下的光化学行为；多亏了芳烃–全氟芳烃 π–π相互作用，其中一些已经显示出给出相应的良好趋势 环丁烷光二聚体的定量收率。溶液和聚合物基体中的光环化都是可逆的，从而提供具有不同顺式-反式立体选择性的相应的对苯二酚。
• Synthesis and Spectroscopic and NLO Properties of “Push-Pull” Structures Incorporating the Inductive Electron-Withdrawing Pentafluorophenyl Group
  作者：Antonio Papagni、Stefano Maiorana、Paola Del Buttero、Dario Perdicchia、Franco Cariati、Elena Cariati、Walter Marcolli

  DOI：10.1002/1099-0690(200204)2002:8<1380::aid-ejoc1380>3.0.co;2-d

  日期：2002.4

  A series of "push-pull" molecules, each incorporating a pentafluorophenyl ring as an inductive accepting group, has been synthesised. The NLO properties of these compounds were measured in solution by EFISH (operating at 1907 nm) and in the solid state by the Kurtz powder technique (at 1907 nm). Values of mubeta, the product of the molecule dipole moment and its first-order hyperpolarizdbility, of up to 200 x 10(-48) esu were obtained.((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).