4-methyl-2,3-diphenylquinoline | 6829-12-5

• 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: 4-methyl-2,3-diphenylquinoline
• 英文别名: 4-Methyl-2,3-diphenylquinoline
• CAS: 6829-12-5
• 化学式: C₂₂H₁₇N
• 分子量: 295.384
• InChiKey: LCBWCPDYNYAAJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  bis(2-phenylquinoline)(acetylacetonate)iridium(III) 、 4-methyl-2,3-diphenylquinoline 以 甘油 为溶剂， 以20%的产率得到Ir(2-phenylquinoline)2(4-methyl-2,3-diphenylquinoline)
  参考文献：
  名称：

  The heteroleptic complexes containing 2,3-diphenylquinoline derivatives as phosphorescent materials

  摘要：

  New types of heteroleptic iridium complexes were designed and synthesized with two different species of chelating ligands (C boolean AND N) in this study. Ir(ppy)(2)(4-Me-2,3-dpq), Ir(ppy)(4-Me-2,3-dpq)(2), Ir(pq)(2)(4-Me-2,3-dpq) and Ir(pq)(4-Me-2,3-dpq)(2) were prepared, where ppy, 4-Me-2,3-dpq and pq represent 2-phenylpyridine, 4-methyl-2,3-diphenylquinoline and 2-phenylquinoline, respectively. According to our previous study, Ir(4-Me-2,3-dpq)(2)(acac) showed orange-red emission at 603 nm with the luminescence efficiency of 8.10 cd/A in electroluminescence (EL) spectra. On the otherhand, Ir(ppy)(2)(acac), a green phosphor, has been known to have an outstanding efficiency of more than 45 cd/A. In order to improve the luminescence efficiency, it is necessary to design a phosphorescent material which is capable of transferring the excited energy efficiently and properly. The heteroleptic Ir(III) complexes containing two different kinds of ligands can have a high luminescence efficiency by intramolecular energy transfer from the energy-absorbing ligand to the luminescent ligand, leading to a decrease in quenching or energy deactivation. Thus, the luminescence characteristics of the iridium, complexes prepared herein were investigated. Ir(ppy)(2)(4-Me-2,3-dpq), Ir(ppy)(4-Me-2,3-dpq)(2), Ir(pq)(2)(4-Me-2,3-dpq) and Ir(pq)(4-Me-2,3-dpq)(2) exhibited the emission maxima at 512, 512, 583, and 584 nm, respectively. Two different light-emitting mechanisms were suggested to explain these phenomena. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jpcs.2007.10.126
• 作为产物：
  描述：

  1-(2-氨基苯基)乙醇 在 C₂H₂F₅NO₄S₂ 、 对甲苯磺酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 4.5h， 生成 4-methyl-2,3-diphenylquinoline
  参考文献：
  名称：

  内部炔烃的无过渡金属碳氨化-轻松获得多取代喹啉

  摘要：

  在协同的布朗斯台德酸基催化剂体系的存在下，实现了未活化的炔烃向高度取代的喹啉的无过渡金属无碳氨化反应。该机制被确认为...

  DOI：

  10.1039/c5cc10460b

文献信息

• Palladium-catalyzed synthesis of polysubstituted quinolines from 2-amino aromatic ketones and alkynes
  作者：Wang Zhou、Jianhua Lei

  DOI：10.1039/c4cc00939h

  日期：——

  A palladium-catalyzed one-pot method for the synthesis of quinolines from commercial or readily available 2-amino aromatic ketones and alkynes is reported for the first time. This transformation offers an alternative method for the synthesis of polysubstituted quinoline.

  首次报道了钯催化的一锅法，由市售或易于获得的2-氨基芳族酮和炔烃合成喹啉。这种转化为合成多取代喹啉提供了另一种方法。
• NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines
  作者：Yang Gao、Simin Yang、Yanping Huo、Qian Chen、Xianwei Li、Xiao-Qiang Hu

  DOI：10.1021/acscatal.1c02055

  日期：2021.7.2

  metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including

  尽管金属-H 催化的加氢胺化方法取得了重大成功，但炔烃的选择性加氢胺化仍然存在相当大的局限性，特别是对于末端炔烃。在此，我们开发了一种高效的 NiH 催化系统，可激活容易获得的炔烃，用于与邻氨基苯甲酸的级联加氢胺化/环化反应。这种温和、操作简单的方案适用于各种炔烃，包括末端和内部、芳基和烷基、缺电子和富电子的炔烃，提供结构多样的喹啉，产率非常高（>80 个例子，高达 93%屈服）。该程序的效用体现在几种天然产物的后期功能化以及抗肿瘤分子墓地宁和三链 DNA 嵌入剂的简明合成中。
• Modular Synthesis of Stereodefined Benzocyclobutene Derivatives via Sequential Cu- and Pd-Catalysis
  作者：Fabien J. T. Talbot、Shibo Zhang、Bishnupada Satpathi、Gareth P. Howell、Gregory J. P. Perry、Giacomo E. M. Crisenza、David J. Procter

  DOI：10.1021/acscatal.1c04496

  日期：2021.12.3

  materials and medicinal chemistry, although general routes for their provision remain underexplored. A modular, divergent, and stereoselective Cu- and Pd-catalyzed assembly/cyclization sequence allows the synthesis of densely functionalized BCBs, from readily accessible imine, allene, and diboron precursors. Preliminary results have identified enantioselective conditions for our protocol and highlighted,

  苯并环丁烯 (BCB) 对材料和药物化学的兴趣越来越大，尽管其提供的一般途径仍未得到充分探索。模块化、发散和立体选择性的 Cu 和 Pd 催化的组装/环化序列允许从容易获得的亚胺、丙二烯和二硼前体合成密集功能化的 BCB。初步结果已经确定了我们协议的对映选择性条件，并强调了，例如，它适用于合成含 BCB 的肽。通过实验条件的简单变化或底物修饰，我们的策略扩展到提供二氢吲哚和喹啉衍生物，适合进一步操作。
• Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines
  作者：Rakesh K. Saunthwal、Monika Patel、Akhilesh K. Verma

  DOI：10.1021/acs.orglett.6b00817

  日期：2016.5.6

  A base promoted, protection-free, and regioselective synthesis of highly functionalized quinolines via [4 + 2] cycloaddition of azadienes (generated in situ from o-aminobenzyl alcohol) with internal alkynes has been discovered. The reaction tolerates a wide variety of functional groups which has been successfully extended with diynes, (2-aminopyridin-3-yl)methanol, and 1,4-bis(phenylethynyl)benzene

  已发现通过氮杂二烯[4 + 2]（由邻氨基苄醇原位生成）与内部炔烃的环加成反应，可促进高度官能化的喹啉的碱促进，无保护和区域选择性的合成。该反应可耐受多种官能团，这些官能团已成功地用二炔，（2-氨基吡啶-3-基）甲醇和1,4-双（苯基乙炔基）苯扩展，得到了（Z）-苯基-2-苯乙烯基喹啉，分别是苯基萘啶和炔烃取代的喹啉。分离出的氮杂二烯中间体和氘标记研究很好地支持了所提出的机理和溶剂的重要作用。
• Introduction of new ancillary ligands to the iridium complexes having 2,3-diphenylquinolinato ligands for OLED
  作者：Hyun Shin Lee、So Youn Ahn、Hyun Sue Huh、Yunkyoung Ha

  DOI：10.1016/j.jorganchem.2009.06.003

  日期：2009.9

  prepared, where R represents C6H5, C6H4CH3 and C6H4Cl. These ligands were chelated to the iridium center to yield a new series of the iridium complexes, Ir(4-Me-2,3-dpq)2(przl-R). The X-ray crystal structure of Ir(4-Me-2,3-dpq)2(przl-C6H4Cl) was determined. The electrochemical and luminescence properties of the iridium complexes were investigated. The effect of the przl-substituents on the emission colors

  我们研究了辅助配体（AL）对其配合物Ir（4-Me-2,3-dpq）2（AL）的发射颜色和发光效率的影响，其中4-Me-2,3-dpq表示4-甲基-2,3-二苯基喹啉基配体。我们期望通过将大的取代基引入配合物中来修饰辅助配体，可能会通过减少T-T ation灭来提高发光效率。此外，一些辅助配体可通过影响轨道混合时的Ir d轨道的能级来有助于其复杂发射颜色的微调。作为新的辅助配位体取代acac，这是铱络合物中的典型AL，吡唑酮基配位体4-R-5-甲基-2-苯基-2,4-二氢-吡唑-3-酮系列（przl-R ），其中R代表C 6 H如图5所示，C 6 H 4 CH 3和C 6 H 4 Cl。这些配体被螯合到铱中心以产生新系列的铱络合物Ir（4-Me-2,3-dpq）2（prz1-R）。测定了Ir（4-Me-2，3-dpq）2（prz1-C 6 H 4 Cl）的X射线晶体结构。研究了铱配合物的电