9H-(4-甲氧基苯基)-3-醛基咔唑 | 84746-66-7

• 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
• 中文名称: 9H-(4-甲氧基苯基)-3-醛基咔唑
• 英文名称: 9-(4-methoxyphenyl)-9H-carbazole-3-carbaldehyde
• 英文别名: 9-(4-methoxyphenyl)carbazole-3-carbaldehyde
• CAS: 84746-66-7
• 化学式: C₂₀H₁₅NO₂
• 分子量: 301.345
• InChiKey: JDYNLKSJRHMLQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  9H-(4-甲氧基苯基)-3-醛基咔唑 在 sodium tetrahydroborate 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.0h， 生成 (E)-5''-(2-(9-(4-methoxyphenyl)-9H-carbazol-3-yl)vinyl)-[2,2':5',2''-terthiophene]-5-carbaldehyde
  参考文献：
  名称：

  Impact of alkoxy chain length on carbazole-based, visible light-driven, dye sensitized photocatalytic hydrogen production

  摘要：

  烷氧基苯基取代的咔唑基金属无机染料被合成，并有效地用于染料敏化的、可见光驱动的光催化制氢。

  DOI：

  10.1039/c5ta04991a
• 作为产物：
  描述：

  4-溴苯甲醚 在 copper(l) iodide 、 L-脯氨酸 、 三氯氧磷 作用下， 以 二甲基亚砜 为溶剂， 反应 169.0h， 生成 9H-(4-甲氧基苯基)-3-醛基咔唑
  参考文献：
  名称：

  Impact of alkoxy chain length on carbazole-based, visible light-driven, dye sensitized photocatalytic hydrogen production

  摘要：

  烷氧基苯基取代的咔唑基金属无机染料被合成，并有效地用于染料敏化的、可见光驱动的光催化制氢。

  DOI：

  10.1039/c5ta04991a

文献信息

• Novel fluorescent carbazole derivative
  申请人：——

  公开号：US20030023099A1

  公开（公告）日：2003-01-30

  The object of this invention is to provide an illuminant, which can easily be produced at low cost. This invention is a carbazole derivative luminescent compound having a carbazole ring skeleton, to the nitrogen atom of which is attached an electron-donating group, and to the carbon atom of which is attached an electron-attracting group at the third position to the nitrogen atom.

  这项发明的目的是提供一种发光剂，可以以低成本轻松生产。这项发明是一种具有咔唑环骨架的咔唑衍生物发光化合物，其中咔唑环骨架的氮原子上连接有一个给电子基团，而连接到该氮原子的第三位置的碳原子上连接有一个吸电子基团。
• Matsuoka, M.; Takao, M.; Kitao, T., Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 182, p. 71 - 79
  作者：Matsuoka, M.、Takao, M.、Kitao, T.、Fujiwara, T.、Nakatsu, K.

  DOI：——

  日期：——
• Red emitting coumarin based 4, 6-disubstituted-3-cyano-2-pyridones dyes – Synthesis, solvatochromism, linear and non-linear optical properties
  作者：Mayuri M.L. Kadam、Dinesh S. Patil、Nagaiyan Sekar

  DOI：10.1016/j.molliq.2018.11.164

  日期：2019.2

  New coumarin fluorescent based D-pi-A-pi-D dyes are synthesized and studied for their optical properties. Their show absorption and emission respectively are in the range of 471-504 nm and 506-550 nm. Viscosity induced emission intensity increase is examined with 0-100% PEG-400 in ethanol MLK 4 is good FMR as compared to the MLK 1-3 due to the presence of extra-pi-conjugation. FMO analysis and Generalized Mulliken Hush analysis show a strong interaction of molecular charge transfer characteristics. The first (alpha), second (beta) and third (gamma) order polarizability of MLK 1-4 are calculated by the solvatochromic technique and corroborated by DFT calculations using CAM-B3LYP/6-31G(d) method. The outcomes found by solvatochromic technique are compared theoretically with DFT using B3LYP/6-31G(d) and CAM-B3LYP/6-31G(d) methods. These methods reveal that, CAMB3LYP/6-31G(d) carry out for calculating alpha, beta, gamma. Photophysical data was also applied to establish the ground and excited state dipole moment ratio using Bakhshiev, Bilot-Kawski, and Liptay functions. Liptay function shows better correlations than the other two functions for all dyes. (C) 2018 Elsevier B.V. All rights reserved.
• <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).
• Design and synthesis of 2-substituted-8-hydroxyquinline zinc complexes with hole-transporting ability for highly effective yellow-light emitters
  作者：Xinhua Ouyang、Guangrong Wang、Heping Zeng、Weiming Zhang、Jing Li

  DOI：10.1016/j.jorganchem.2009.06.022

  日期：2009.10

  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.