(E)-2-[2-(9-(4-methylphenyl)-9H-carbazol-3-yl)vinyl]quinolin-8-ol | 1192827-48-7

• 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: (E)-2-[2-(9-(4-methylphenyl)-9H-carbazol-3-yl)vinyl]quinolin-8-ol
• 英文别名: 2''-(2'-(9-p-tolyl-9H-carbazol-3-yl)-vinyl)-8-hydroxyquinoline；2-[(E)-2-[9-(4-methylphenyl)carbazol-3-yl]ethenyl]quinolin-8-ol
• CAS: 1192827-48-7
• 化学式: C₃₀H₂₂N₂O
• 分子量: 426.517
• InChiKey: JHKOEOSOCSKTNL-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-[2-(9-(4-methylphenyl)-9H-carbazol-3-yl)vinyl]quinolin-8-ol 、 zinc(II) acetate dihydrate 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以72.8%的产率得到bis((E)-2-(2-(9-p-tolyl-9H-carbazol-3-yl)vinyl)quinolin-8-olato)zinc
  参考文献：
  名称：

  Design and synthesis of 2-substituted-8-hydroxyquinline zinc complexes with hole-transporting ability for highly effective yellow-light emitters

  摘要：

  Four multifunctional 8-hydroxyquinoline derivatives were designed and synthesized, their structures were identified by FT-IR, H-1 NMR, MS and elemental analysis. Among them are (E)-2-(2-(9-(4-methoxyphenyl)-9H-carbazol-3-yl)vinyl) quinolato-zinc (1), (E)-2-(2-(9-p-tolyl-9H-carbazol-3-yl)vinyl)quinolato-zinc (2), (E)-2-(2-(9H-fluoren-2-yl)vinyl)quinolato-zinc (3), and (E)-2-(2-(phenanthren-9-yl)vinyl)quinolato-zinc (4). The electroluminescence (EL) and hole-transporting characteristics of these materials were investigated on four configurations: (A) ITO/2-TNATA/NPB/1, 2, 3 or 4/Alq(3)/LiF/Al; (B) ITO/2-TNATA/NPB/1, 2, 3 or 4/LiF/Al; (C) ITO/2-TNATA/1, 2, 3 or 4/Alq(3)/LiF/Al; and (D) ITO/2-TNATA/1 or 2/NPB/Alq(3)/LiF/Al. The maximum luminescence and current efficiencies of are 3556 cd m(-2) (at 13 V) and 2.17 cd A(-1) ( at 9 V) for compound 2, 4624 cd m(-2) (at 15 V) and 2.1 cd A(-1) (at 7 V) for compound 3, and 3164 cd m(-2) ( at 14 V) and 1.83 cd A(-1) (at 13 V) for compound 4 in the configuration D, respectively, indicating that they are good multifunctional materials with strong hole-transporting abilities and luminescence properties. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.06.022
• 作为产物：
  描述：

  8-羟基喹哪啶 、 9-(p-tolyl)-9H-carbazole-3-carbaldehyde 在 乙酸酐 作用下， 反应 40.0h， 以62.5%的产率得到(E)-2-[2-(9-(4-methylphenyl)-9H-carbazol-3-yl)vinyl]quinolin-8-ol
  参考文献：
  名称：

  Design and synthesis of 2-substituted-8-hydroxyquinline zinc complexes with hole-transporting ability for highly effective yellow-light emitters

  摘要：

  Four multifunctional 8-hydroxyquinoline derivatives were designed and synthesized, their structures were identified by FT-IR, H-1 NMR, MS and elemental analysis. Among them are (E)-2-(2-(9-(4-methoxyphenyl)-9H-carbazol-3-yl)vinyl) quinolato-zinc (1), (E)-2-(2-(9-p-tolyl-9H-carbazol-3-yl)vinyl)quinolato-zinc (2), (E)-2-(2-(9H-fluoren-2-yl)vinyl)quinolato-zinc (3), and (E)-2-(2-(phenanthren-9-yl)vinyl)quinolato-zinc (4). The electroluminescence (EL) and hole-transporting characteristics of these materials were investigated on four configurations: (A) ITO/2-TNATA/NPB/1, 2, 3 or 4/Alq(3)/LiF/Al; (B) ITO/2-TNATA/NPB/1, 2, 3 or 4/LiF/Al; (C) ITO/2-TNATA/1, 2, 3 or 4/Alq(3)/LiF/Al; and (D) ITO/2-TNATA/1 or 2/NPB/Alq(3)/LiF/Al. The maximum luminescence and current efficiencies of are 3556 cd m(-2) (at 13 V) and 2.17 cd A(-1) ( at 9 V) for compound 2, 4624 cd m(-2) (at 15 V) and 2.1 cd A(-1) (at 7 V) for compound 3, and 3164 cd m(-2) ( at 14 V) and 1.83 cd A(-1) (at 13 V) for compound 4 in the configuration D, respectively, indicating that they are good multifunctional materials with strong hole-transporting abilities and luminescence properties. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.06.022

文献信息

• <i>In Vitro</i>Studies on the Antioxidant and Protective Effect of 2-Substituted -8-Hydroxyquinoline Derivatives Against H₂O₂-Induced Oxidative Stress in BMSCs
  作者：Ting-Ting Wang、Gong-Chang Zeng、Xi-Can Li、He-Ping Zeng

  DOI：10.1111/j.1747-0285.2009.00925.x

  日期：2010.2

  Novel 2‐vinyl‐8‐hydroxyquinoline derivatives as potential antioxidants and regulators of H2O2‐induced oxidative stress in rat bone marrow mesenchymal stem cells (MSCs) are first reported. The antiradical properties and the reducing power of these compounds were assessed using 2, 2‐diphenyl‐1‐picrylhydrazyl (DPPH) and auto‐oxidation of pyrogallol method, respectively. The activity against lipid peroxidation was determined using ammonium thiocyanate method. The results revealed that introduction of electron‐donating groups at 2nd position decreased the antioxidant activities of 8‐hydroxyquinoline derivatives. In addition, compound 4, the structure of which is similar to melatonin, exhibited superior antioxidant activities in scavenging DPPH free radical, ˙O2 free radical, and anti‐LPO activities. Except for compounds 7, 12, and 15, the other compounds exhibited a stimulatory effect on MSCs growth. Using hydrogen peroxide (H2O2), we also investigated the protective efficacy of 2‐vinyl‐8‐hydroxyquinoline derivatives against oxidative stress‐induced cell death of MSCs. Cell viability assayed by MTT method indicated that exposure of MSCs cultures to hydrogen peroxide resulted in a concentration‐dependent decrease in cell viability, and compounds 4 and 5 at given concentration (2.62 × 10−3 m) could protect MSCs against H2O2‐induced oxidative stress in bone mesenchymal stem cell (BMSCs).