2-[2-(2,4-Difluorophenyl)ethynyl]-1-(2-ethylhexyl)indole-3-carbaldehyde | 1352798-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-[2-(2,4-Difluorophenyl)ethynyl]-1-(2-ethylhexyl)indole-3-carbaldehyde
• CAS: 1352798-24-3
• 化学式: C₂₅H₂₅F₂NO
• 分子量: 393.476
• InChiKey: WEMGRMXCLCXFJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(2,4-Difluorophenyl)ethynyl]-1-(2-ethylhexyl)indole-3-carbaldehyde 在 叔丁胺 作用下， 以 甲苯 为溶剂， 以60%的产率得到3-(2,4-difluorophenyl)-5-(2-ethylhexyl)-pyrido[4,3-b]indole
  参考文献：
  名称：

  Thermally Induced Defluorination during a mer to fac Transformation of a Blue-Green Phosphorescent Cyclometalated Iridium(III) Complex

  摘要：

  The new homoleptic tris-cyclometalated [Ir((CN)-N-boolean AND)(3)] complexes mer-8, fac-8, and fac-9 incorporating gamma-carboline ligands are reported. Reaction of 3-(2,4-difluorophenyl)-5-(2-ethylhexyl)-pyrido[4,3-b]indole 6 with iridium(III) chloride under standard cyclometalating conditions gave the homoleptic complex mer-8 in 63% yield. The X-ray crystal structure of mer-8 is described. The Ir-C and Ir-N bonds show the expected bond length alternations for the differing trans influence of phenyl and pyridyl ligands. mer-8 quantitatively isomerized to fac-8 upon irradiation with UV light. However, heating mer-8 at 290 degrees C in glycerol led to an unusual regioselective loss of one fluorine atom from each of the ligands, yielding fac-9 in 58% yield. fac-8 is thermally very stable: no decomposition was observed when fac-8 was heated in glycerol at 290 degrees C for 48 h. The gamma-carboline system of fac-8 enhances thermal stability compared to the pyridyl analogue fac-Ir(46dfppy)(3) 10, which decomposes extensively upon being heated in glycerol at 290 degrees C for 2 h. Complexes mer-8, fac-8, and fac-9 are emitters of blue-green light (lambda(em)(max) = 477, 476, and 494 nm, respectively). The triplet lifetimes for fac-8 and fac-9 are similar to 4.5 Its at room temperature; solution On values are 0.31 and 0.22, respectively.

  DOI：

  10.1021/ic201655n
• 作为产物：
  描述：

  1-(2-ethylhexyl)-indole-3-carboxaldehyde 在 N-甲基哌嗪 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 碘 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-[2-(2,4-Difluorophenyl)ethynyl]-1-(2-ethylhexyl)indole-3-carbaldehyde
  参考文献：
  名称：

  Thermally Induced Defluorination during a mer to fac Transformation of a Blue-Green Phosphorescent Cyclometalated Iridium(III) Complex

  摘要：

  The new homoleptic tris-cyclometalated [Ir((CN)-N-boolean AND)(3)] complexes mer-8, fac-8, and fac-9 incorporating gamma-carboline ligands are reported. Reaction of 3-(2,4-difluorophenyl)-5-(2-ethylhexyl)-pyrido[4,3-b]indole 6 with iridium(III) chloride under standard cyclometalating conditions gave the homoleptic complex mer-8 in 63% yield. The X-ray crystal structure of mer-8 is described. The Ir-C and Ir-N bonds show the expected bond length alternations for the differing trans influence of phenyl and pyridyl ligands. mer-8 quantitatively isomerized to fac-8 upon irradiation with UV light. However, heating mer-8 at 290 degrees C in glycerol led to an unusual regioselective loss of one fluorine atom from each of the ligands, yielding fac-9 in 58% yield. fac-8 is thermally very stable: no decomposition was observed when fac-8 was heated in glycerol at 290 degrees C for 48 h. The gamma-carboline system of fac-8 enhances thermal stability compared to the pyridyl analogue fac-Ir(46dfppy)(3) 10, which decomposes extensively upon being heated in glycerol at 290 degrees C for 2 h. Complexes mer-8, fac-8, and fac-9 are emitters of blue-green light (lambda(em)(max) = 477, 476, and 494 nm, respectively). The triplet lifetimes for fac-8 and fac-9 are similar to 4.5 Its at room temperature; solution On values are 0.31 and 0.22, respectively.

  DOI：

  10.1021/ic201655n