9-(2,4,6-三甲基苯基)咔唑 | 327162-78-7

• 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: 9-(2,4,6-三甲基苯基)咔唑
• 英文名称: 9-mesitylcarbazole
• 英文别名: 9-(2,4,6-Trimethylphenyl)-9H-carbazole；9-(2,4,6-trimethylphenyl)carbazole
• CAS: 327162-78-7
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: RCSVFOIVLUAFFP-UHFFFAOYSA-N

物化性质

• 沸点：
  453.2±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-(2,4,6-三甲基苯基)咔唑 在 乙酸酐 、 copper(II) nitrate 、 溶剂黄146 作用下， 反应 12.0h， 以84%的产率得到C₂₁H₁₇N₃O₄
  参考文献：
  名称：

  Metal Coordination Guided Formation of Discrete Neutral Three-Component Hydrogen-Bonded Architectures

  摘要：

  Interesting molecular architectures were obtained by combining heterodimeric quadruple hydrogen-bonding and neutral metal corner braces. The selection of cyclic and noncyclic aggregates from a random mixture of two-component assemblies has been achieved through metal coordination and careful adjustment of monomer rigidity and dimensions.

  DOI：

  10.1021/acs.orglett.0c03397
• 作为产物：
  描述：

  2,4,6-三甲基-N-苯基苯胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 新铜试剂 、 碘 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 methyloxirane 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 44.0h， 生成 9-(2,4,6-三甲基苯基)咔唑
  参考文献：
  名称：

  可见光介导的咔唑合成

  摘要：

  光合制备的ñ -芳基-和ñ -烷基轴承咔唑利用连续流，可见光，和原位形成的铜基增敏剂（参照图片）。该方法温和高效，可直接合成具有不同取代基，杂环和复杂碳结构的多种咔唑。

  DOI：

  10.1002/anie.201306920

文献信息

• Transition-Metal-Free Synthesis of Carbazoles and Indoles by an S_NAr-Based “Aromatic Metamorphosis” of Thiaarenes
  作者：M. Bhanuchandra、Kei Murakami、Dhananjayan Vasu、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1002/anie.201503671

  日期：2015.8.24

  dibenzothiophenes, undergo nucleophilic aromatic substitution with anilines intermolecularly and then intramolecularly to yield the corresponding carbazoles in a single operation. The “aromatic metamorphosis” of dibenzothiophenes into carbazoles does not require any heavy metals. This strategy is also applicable to the synthesis of indoles. Since electron‐deficient thiaarene dioxides exhibit interesting reactivity

  通过母体二苯并噻​​吩的氧化容易制备的二苯并噻吩二氧化物在一次操作中在分子内然后在分子内经历苯胺的亲核芳香取代，然后生成分子内相应的咔唑。二苯并噻吩向咔唑的“芳香变形”不需要任何重金属。该策略也适用于吲哚的合成。由于缺电子的硫杂芳烃二氧化物表现出有趣的反应性，而相应的富电子氮杂芳烃则未观察到，因此，二氧化硫杂ar特定反应与基于S N Ar的芳族变态反应的结合，使得无过渡金属的结构成为可能。难以制备咔唑。
• Carbazole Synthesis by Platinum-catalyzed C–H Functionalizing Reaction Using Water as Reoxidizing Reagent
  作者：Mitsuru Yamamoto、Seijiro Matsubara

  DOI：10.1246/cl.2007.172

  日期：2007.1

  Treatment of 1-aminobiphenyl and diphenylamine with catalytic amount of Pt/C in hydrothermal water (250 °C, 4 MPa) affords 9H-carbazole in good yield. In this catalytic cycle, water works as reoxidizing reagent for platinum catalyst.

  在高温水热条件下（250°C，4 MPa），使用少量Pt/C催化剂处理1-氨基联苯和二苯胺，可高产率地获得9H-咔唑。在这一催化循环中，水作为铂催化剂的再氧化剂。
• Assessing Carbazole Derivatives as Single-Electron Photoreductants
  作者：Tyler D. Weinhold、Natalie A. Reece、Kevin Ribeiro、Maredh Lopez Ocasio、Noelle Watson、Kenneth Hanson、Ashley R. Longstreet

  DOI：10.1021/acs.joc.2c02312

  日期：2022.12.16

  The electron-donating capabilities of carbazoles have stimulated interest in their use as photoinduced single-electron reductants. Due to the modularity of the carbazole, a further broadening and understanding of their reactivity could be achieved by manipulating the structure. Herein, eight carbazole derivatives were synthesized, characterized, and assessed as single-electron photoreductants in the

  咔唑的给电子能力激发了人们对其用作光致单电子还原剂的兴趣。由于咔唑的模块化，可以通过操纵结构来进一步拓宽和理解它们的反应性。在此，合成、表征和评估了八种咔唑衍生物作为单电子光还原剂在芳基卤化物的加氢脱卤和N-甲基吡咯的芳基化中的作用。
• Carbazolyl Nitrenium Cations: Generation and Reactions
  作者：Dariusz Bogdal

  DOI：10.3987/com-00-9027

  日期：——

  Carbazolyl nitrenium cations were generated during the thermolysis and photolysis of 1-carbazol-9-yl-2,4,6-triphenylpyridinium (Py+-Cz) tetranuoroborate in 2,2,2-trinuoroethanold- and TFA-mesitylene mixtures. The thermolysis of Py+-Cz in TFA-mesitylene mixture gave 9-mesitylcarbazole in good yield along with carbazole, non-symmetrical mesitylene dimer, 2,4,6-triphenylpyridine, and a small amount of 9-(3,5-dimethylbenzyl)carbazole, whereas the thermolysis in trifluoroethanol - mesitylene mixture gave 9-mesitylcarbazole as the main product along with carbazole and 2,4,6-triphenylpyridine. The pro duct distributions lead to two major conclusions. First, photolysis and thermolysis of Py+-Cz salt produce nitrenium ions that can be in singlet or triplet state dependant on the reaction conditions. Second, the carbazolyl nitrenium ion exhibits singlet state in the ground state.
• Photochemical Synthesis of Carbazoles Using an [Fe(phen)₃](NTf₂)₂/O₂ Catalyst System: Catalysis toward Sustainability
  作者：Shawn Parisien-Collette、Augusto C. Hernandez-Perez、Shawn K. Collins

  DOI：10.1021/acs.orglett.6b02456

  日期：2016.10.7

  An increasingly sustainable photochemical synthesis of carbazoles was developed using a catalytic system of Fe(phen)(3)(NTf2)(2)/O-2 under continuous flow conditions and was demonstrated on gram scale using a numbering-up strategy. Photocyclization of triaryl and diarylamines into the corresponding carbazoles occurs in general in higher yields than with previously developed photocatalysts.