9-(9'-acridyl)carbazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-(9'-acridyl)carbazole
• 英文别名: 9-(9H-carbazol-9-yl)acridine；9-carbazol-9-ylacridine
• 化学式: C₂₅H₁₆N₂
• 分子量: 344.415
• InChiKey: MHUIYPXRENZOOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氨基苯甲醛 在 copper(l) iodide 、 硫酸 、 potassium carbonate 、 caesium carbonate 、 溶剂黄146 作用下， 以 二丁醚 、 二甲基亚砜 为溶剂， 反应 48.5h， 生成 9-(9'-acridyl)carbazole
  参考文献：
  名称：

  2-氨基苯甲醛，具有生物活性的a啶和a啶的常见前体

  摘要：

  从共同的底物2-氨基苯甲醛开始，制备了cr啶和a啶酮。前者是通过铜催化的N-芳基化反应，然后进行酸介导的环化反应而以高收率产生的，而后者是通过双重铜催化的N-芳基化，然后在相同反应条件下环化。此外，a啶通过依赖于锂锌碱进行去金属化并转化为相应的4-碘衍生物，其与吡咯烷酮和吡唑参与铜催化的偶联。最后，将吡唑，吲哚和咔唑添加到裸a啶的9位上得到改善。虽然在黑素瘤细胞生长抑制中注意到了适度的生物学活性，但新制备的化合物具有有趣的光物理性质，这些性质在初步研究中已进行了评估。

  DOI：

  10.1016/j.tet.2020.131435

文献信息

• Solid State Bimolecular Photoreaction in a Simple Polycrystalline Mixture of Acridine and Carbazole
  作者：Hideko Koshima

  DOI：10.1080/10587250108023726

  日期：2001.2.1

  Irradiation of a simple polycrystalline mixture of acridine and carbazole gave a condensation product as a sole product.
• On the TICT Mechanism of 9,9′-Biaryl Compounds
  作者：Javier Catalán、Cristina Díaz、Vicenta López、Pilar Pérez、Rosa María Claramunt

  DOI：10.1002/(sici)1099-0690(199808)1998:8<1697::aid-ejoc1697>3.0.co;2-w

  日期：1998.8

  The UV/Vis absorption and fluorescence spectra for 9,9'-biacridinyl (BAC) and 9-(9'-acridyl)carbazole (C9AC) were recorded in approximately 50 different solvents. The analysis of the solvatochromic behaviour of the two chromophores, in terms of both polarity and polarizability (SPP), revealed that TICT emission in C9AC prevails only in solvents with SPP greater than or equal to 0.63, while that in BAC predominates throughout the solvent range studied [from 2-methylbutane (SPP = 0.479) to DMSO (SPP = 1.0)]. The peculiar behaviour of BAC suggests that the chromophore requires no cooperation from the solvent to trigger its TICT mechanism. Various hypotheses usually employed in analysing the TICT mechanism of biaryl compounds, including model emissions used to deconvolute spectra, the variation of TICT emission with the difference in redox potential between the chromophores involved, etc., are discussed.
• Boyer, Gerard; Claramunt, Rosa M.; Elguero, Jose, Journal of the Chemical Society. Perkin transactions II, 1993, # 4, p. 757 - 766
  作者：Boyer, Gerard、Claramunt, Rosa M.、Elguero, Jose、Fathalla, Mohamed、Foces-Foces, Concepcion、et al.

  DOI：——

  日期：——
• DMITRIEVA, L. L.;SARAULOVA, G. I.;KUROV, G. N., VINITI 1853-B
  作者：DMITRIEVA, L. L.、SARAULOVA, G. I.、KUROV, G. N.

  DOI：——

  日期：——
• 2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities
  作者：Sarah Zeghada、Ghenia Bentabed-Ababsa、Olivier Mongin、William Erb、Laurent Picot、Valérie Thiéry、Thierry Roisnel、Vincent Dorcet、Florence Mongin

  DOI：10.1016/j.tet.2020.131435

  日期：2020.9

  By starting from a common substrate, 2-aminobenzaldehyde, both acridines and acridones were prepared. The former were generated in high yields by copper-catalyzed N-arylation followed by acid-mediated cyclization while the latter were obtained by double copper-catalyzed N-arylation followed by cyclization under the same reaction conditions. Moreover, acridine was subjected to deprotometalation by recourse

  从共同的底物2-氨基苯甲醛开始，制备了cr啶和a啶酮。前者是通过铜催化的N-芳基化反应，然后进行酸介导的环化反应而以高收率产生的，而后者是通过双重铜催化的N-芳基化，然后在相同反应条件下环化。此外，a啶通过依赖于锂锌碱进行去金属化并转化为相应的4-碘衍生物，其与吡咯烷酮和吡唑参与铜催化的偶联。最后，将吡唑，吲哚和咔唑添加到裸a啶的9位上得到改善。虽然在黑素瘤细胞生长抑制中注意到了适度的生物学活性，但新制备的化合物具有有趣的光物理性质，这些性质在初步研究中已进行了评估。

表征谱图