9-(3-fluorophenyl)-9H-carbazole

• 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: 9-(3-fluorophenyl)-9H-carbazole
• 英文别名: 9-(3-Fluorophenyl)-9H-carbazole；9-(3-fluorophenyl)carbazole
• 化学式: C₁₈H₁₂FN
• 分子量: 261.298
• InChiKey: YCPDJJWGODNLJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-硝基联苯 在 盐酸 、 copper diacetate 、 sodium carbonate 、 一水合肼 、 乙二醇 、 间氯过氧苯甲酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 19.33h， 生成 9-(3-fluorophenyl)-9H-carbazole
  参考文献：
  名称：

  通过将一锅铜催化的胺插入环状二苯并碘鎓中来合成咔唑，作为生成类似药物的化学文库的策略

  摘要：

  AbstractCarbazoles have attracted high interest among synthetic chemists due to their unique structural features and potential pharmacological activities. Compared to linear aryliodoniums, cyclic diphenyleneiodoniums are more inert and have not attracted much attention to their application as building blocks. Employing our synthetic strategy, diversified carbazoles can be efficiently obtained from a single cyclic diphenyleneiodonium under mild conditions. The reactions catalyzed by copper(II) acetate have provided a variety of carbazoles in modest to good yields with a broad range of amines including anilines, aliphatic amines and sulfonamides. Moreover, one of the obtained carbazoles has displayed an outstanding ability to protect HT‐22 neuronal cells from the damage induced by neurotoxins glutamate and homocysteic acid.magnified image

  DOI：

  10.1002/adsc.201300271

文献信息

• ORGANIC LIGHT-EMITTING DEVICE AND COMPOUND
  申请人：Samsung Electronics Co., Ltd.

  公开号：US20180166634A1

  公开（公告）日：2018-06-14

  An organic light-emitting device including a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the emission layer includes a fluorescent compound represented by a specific formula described in the specification.

  一种有机发光器件，包括第一电极，面向第一电极的第二电极，以及设置在第一电极和第二电极之间的有机层，其中有机层包括一个发射层，该发射层包括一个在规范中描述的特定公式代表的荧光化合物。
• Copper/β-diketone-catalysed N-arylation of carbazoles
  作者：Fei Chen、Ning Liu、Enhui Ji、Bin Dai

  DOI：10.1039/c5ra07690k

  日期：——

  A copper/β-diketone-catalysedN-arylation of carbazoles with aryl iodides is developed with broad substrate applicability and moderate to good yields.

  使用铜/β-二酮催化剂对碳酰胺与芳基碘化物进行N-芳基化反应，具有广泛的底物适用性和中等至良好的产率。
• Palladium-catalyzed C–H bond activation for the assembly of <i>N</i>-aryl carbazoles with aromatic amines as nitrogen sources
  作者：Xiaobing Liu、Heyun Sheng、Yao Zhou、Qiuling Song

  DOI：10.1039/c9cc09493h

  日期：——

  A convenient and efficient palladium-catalyzed C-H bond activation for the assembly of N-aryl carbazole is reported, in which two C-N bonds were formed under one set of conditions. The desired carbazoles were achieved in decent yields with a wide substrate scope by utilizing readily available 2-iodo biphenyls and aromatic amines as starting materials.

  报道了一种用于组装N-芳基咔唑的便捷且有效的钯催化的CH键活化，其中在一组条件下形成了两个CN键。通过使用容易获得的2-碘联苯和芳族胺作为起始原料，可以在宽范围的底物范围内以适当的收率获得所需的咔唑。
• Base-Promoted SNAr Reactions of Fluoro- and Chloroarenes as a Route to N-Aryl Indoles and Carbazoles
  作者：Muhammad Iqbal、Hina Mehmood、Jiaying Lv、Ruimao Hua

  DOI：10.3390/molecules24061145

  日期：——

  KOH/DMSO-promoted C-N bond formation via nucleophilic aromatic substitution (SNAr) between chloroarenes or fluoroarenes with indoles and carbazole under transition metal-free conditions affording the corresponding N-arylated indoles and carbazoles has been developed.

  通过KOH/DMSO促进的无过渡金属条件下，氯代芳烃或氟代芳烃与吲哚和咔唑之间的亲核芳基取代反应（SNAr），形成C-N键，从而合成相应的N-芳基化吲哚和咔唑。
• Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity
  作者：Daqian Zhu、Meihui Chen、Min Li、Bingling Luo、Yang Zhao、Peng Huang、Fengtian Xue、Simona Rapposelli、Rongbiao Pi、Shijun Wen

  DOI：10.1016/j.ejmech.2013.07.029

  日期：2013.10

  Carbazole moiety is an important scaffold with a variety of biological applications, for example, anti-oxidative stress. Our previous synthesized carbazoles were screened for their neuroprotective properties against two individual oxidative stresses. Some of the new carbazole derivatives were observed with modest to good neuroprotective effects on neuronal cells HT22 against cell injury induced by glutamate or homocysteic acid (HCA). Substituents introduced to the carbazole ring system play crucial roles in their biological activities. In particular, a bulky group favors the neuroprotective activity of the compounds. One of the new compounds, 6, showed the best neuroprotective effects, which might result from its anti-oxidative activity with a GSH-independent mechanism. These findings might provide an alternative strategy for the development of novel carbazole derivatives for the treatment of CNS diseases such as Alzheimer's disease. (C) 2013 Elsevier Masson SAS. All rights reserved.