2-methoxy-9-phenyl-9H-carbazole | 1357929-88-4

• 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: 2-methoxy-9-phenyl-9H-carbazole
• 英文别名: 2-methoxy-9-phenylcarbazole
• CAS: 1357929-88-4
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: WJWUCWGMYCKNJT-UHFFFAOYSA-N

物化性质

• 沸点：
  449.7±27.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methoxy-9-phenyl-9H-carbazole 在 2-吡啶甲酸 、 potassium phosphate 、 copper(l) iodide 、 氢溴酸 作用下， 以 二甲基亚砜 为溶剂， 反应 96.0h， 生成 2-(5-Imidazol-1-ylpyridin-3-yl)oxy-9-phenylcarbazole
  参考文献：
  名称：

  有机电致发光装置及用于有机电致发光装置的有机金属化合物

  摘要：

  本申请涉及由式1表示的有机金属化合物和有机电致发光装置，其中所述有机电致发光装置包含在发射层中的所述由式1表示的有机金属化合物，以实现高效率、低驱动电压、高亮度和长寿命：式1

  公开号：

  CN112794869A
• 作为产物：
  描述：

  4-甲氧基-2-硝基联苯 在 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 、 亚磷酸三乙酯 作用下， 以 二甲基亚砜 为溶剂， 反应 17.0h， 生成 2-methoxy-9-phenyl-9H-carbazole
  参考文献：
  名称：

  Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials

  摘要：

  New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and F-19 NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.

  DOI：

  10.1021/jo2020906

文献信息

• Palladium-Catalyzed Intramolecular C–H Arylation of Arenes Using Tosylates and Mesylates as Electrophiles
  作者：Christine S. Nervig、Peter J. Waller、Dipannita Kalyani

  DOI：10.1021/ol302166n

  日期：2012.9.21

  paper describes a method for the palladium catalyzed intramolecular C–H arylation using tosylates and mesylates as electrophiles. The transformation is efficient for the synthesis of various heterocyclic motifs including furans, carbazoles, indoles, and lactams. Additionally, a protocol for the one-pot sequential tosylation/arylation of phenol derivatives is presented.

  本文介绍了一种使用甲苯磺酸盐和甲磺酸盐作为亲电子试剂进行钯催化的分子内CH-H芳基化的方法。该转化对于合成各种杂环基序有效，包括呋喃，咔唑，吲哚和内酰胺。另外，提出了一种用于苯酚衍生物的一锅顺序甲苯磺酸化/芳基化的方案。
• Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV‐ and Visible‐Light Methods in Continuous Flow
  作者：Augusto C. Hernandez‐Perez、Antoine Caron、Shawn K. Collins

  DOI：10.1002/chem.201502661

  日期：2015.11.9

  An evaluation of both a visible‐light‐ and UV‐light‐mediated synthesis of carbazoles from various triarylamines with differing electronic properties under continuous‐flow conditions has been conducted. In general, triarylamines bearing electron‐rich groups tend to produce higher yields than triarylamines possessing electron‐withdrawing groups. The incorporation of nitrogen‐based heterocycles, as well

  在连续流动条件下，对可见光和紫外光介导的由具有不同电子性质的各种三芳基胺合成咔唑进行了评估。通常，带有富电子基团的三芳基胺往往比具有吸电子基团的三芳基胺产生更高的产率。在咔唑骨架中掺入氮基杂环以及含卤素的芳烃的耐受性良好，通常在紫外光和可见光（光氧化还原）方法之间观察到合成有用的互补性。
• 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。
• Cu2O-Catalyzed Ullmann-type C N cross-coupling reaction of carbazole and aryl chlorides
  作者：Baiyao Zhu、Wenfang Xiong、Xiaobin Tan、Wanqing Wu、Huanfeng Jiang

  DOI：10.1016/j.tetlet.2022.154140

  日期：2022.10

  A copper-catalyzed Ullmann-type CN cross-coupling reaction of carbazole with aryl chlorides has been developed employing N,N′-bis(thiophene-2-ylmethyl)oxalamide as ligand. The reaction proceeds at 140 °C with Cs2CO3 as the base in DMSO/MeCN to afford N-arylcarbazole in good to excellent yields. Both the heteroaromatic ring and amide structures in ligands are important for their efficiency.

  以N , N'-双(噻吩-2-基甲基)草酰胺为配体,开发了咔唑与芳基氯化物的铜催化乌尔曼型CN交叉偶联反应。该反应在 140 °C 下以 Cs 2 CO 3作为碱在 DMSO/MeCN 中进行，以良好至优异的收率得到N-芳基咔唑。配体中的杂芳环和酰胺结构对其效率都很重要。
• Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials
  作者：Brett A. Kamino、Bridget Mills、Christopher Reali、Michael J. Gretton、Michael A. Brook、Timothy P. Bender

  DOI：10.1021/jo2020906

  日期：2012.2.17

  New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and F-19 NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.