2-(3-fluorophenyl)-4-phenylquinoline

• 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: 2-(3-fluorophenyl)-4-phenylquinoline
• 英文别名: 2-(3-Fluorophenyl)-4-phenylquinoline
• 化学式: C₂₁H₁₄FN
• 分子量: 299.347
• InChiKey: ASSMRCSTUORAIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(1-(3-fluorophenyl)-3-phenylprop-2-yn-1-yl)aniline 在 montmorillonite clay doped with CuCl 、 air 作用下， 反应 0.1h， 以72%的产率得到2-(3-fluorophenyl)-4-phenylquinoline
  参考文献：
  名称：

  Microwave promoted one-pot preparation of fluorinated propargylamines and their chemical transformation

  摘要：

  A series of fluorinated propargylamines have been synthesized from the one-pot three-component reaction of fluorobenzaldehyde, aniline and phenylacetylene under solvent-free and microwave irradiation. The fluorinated propargylamines were then further transformed to chalcones or quinoline derivatives respectively depending on the different structures of propargylamines. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.08.005

文献信息

• Synthesis of multi-functionalized quinolines and 1,2-dihydroquinolines through FeCl₃ -mediated reactions of carbonyl compounds with 2-vinylanilines
  作者：Sha Liu、Gaoqiang Li、Feng Xu

  DOI：10.1002/jccs.201800001

  日期：2018.7

  A facile and efficient approach toward the synthesis of functionalized quinolines and 1,2‐dihydroquinolines from carbonyl compounds and 2‐vinylanilines is described. The protocol utilizes the nonhazardous and less expensive FeCl3 as catalyst with wide functional group tolerance and avoiding heavy metal impurities in the products.

  描述了一种从羰基化合物和2-乙烯基苯胺合成官能化喹啉和1,2-二氢喹啉的简便有效方法。该方案使用无害且价格便宜的FeCl 3作为催化剂，具有宽泛的官能团耐受性，并避免了产品中的重金属杂质。
• One-Pot Synthesis of 2-Arylquinolines via in situ Acid Catalysis
  作者：Lei Feng、Chen Ma、Qiang Han、Shichen Li、Zepeng Cai、Chengcheng Ding

  DOI：10.1055/a-1889-9354

  日期：2022.11

  A simple, efficient, and practical protocol is reported, allowing quick access to diverse 2-arylquinolines from 2-vinylanilines and benzyl halides. This reaction is additive and metal catalyst-free with only solvent needed. A preliminary mechanistic investigation discloses the driving force comes from the in situ released HBr, which catalyzes the subsequent cyclization. The present synthetic route

  报告了一种简单、有效且实用的方案，允许从 2-乙烯基苯胺和苄基卤化物中快速获取各种 2-芳基喹啉。该反应不含添加剂和金属催化剂，仅需要溶剂。初步的机理研究表明，驱动力来自原位释放的 HBr，它催化了随后的环化。目前的合成路线具有高官能团耐受性和简单的后处理。各种 2-芳基喹啉的收率高达 96%。
• Synthesis and Characterization of Red-emitting Iridium Complexes of 5′-Substituted 2,4-diphenylquinolines
  作者：Seung-Chan Lee、Young Sik Kim

  DOI：10.1080/15421400903065770

  日期：2009.9.3

  To examine the substituent effect, 5'-substituted 2,4-diphenylquinoline (dpq) ligands and their iridium complexes, Ir(dpq)(2)(acac), Ir(dpq-5F)(2)(acac), Ir(dpq-5CH(3))(2)(acac) and Ir(dpq-5OCH3)(2)(acac), were synthesized and prepared, and the photophysical properties were investigated for red electro-phosphorescent materials. The 5'-substituted phenyl ring generated 3'-positon and 5'-position isomers. However, the 5'-position of the phenyl ring is more stable than the 3'-position due to steric effects. The maximum emission wavelengths of Ir(dpq)(2)(acac), Ir(dpq-5F)(2)(acac), Ir(dpq-5CH(3))(2)(acac) and Ir(dpq-5OCH(3))(2)(acac) were found at 612, 606, 616, 606 nm, respectively. The emission spectrum of Ir(dpq-5CH(3))(2)(acac) was red shifted compared to that of Ir(dpq)(2)(acac) because the methyl group substituted on the 5'-position of the phenyl ring is an electron donating group. Ir(dpq-5F)(2)(acac) shows highly efficient and blue-shifted luminescence because the electron withdrawing group (-F) substitute on the 5'-position of the phenyl ring lowered the HOMO level slightly. Hence MLCT coupling is increased and blue shifted luminescence by 6 nm was observed compared to Ir(dpq)(2)(acac). Especially, Ir(dpq-5OCH(3))(2)(acac) shows blue-shifted phosphorescence due to the effect of the electron withdrawing methoxyphenyl group onto the iridium atom. This destabilized the MLCT state and leads to an increased in the emission energy.
• Heteroleptic Iridium(III) Complexes with Phenylpridine and Diphenylquinoline Derivative Ligands
  作者：Yong Hwan Park、Gui Youn Park、Young Sik Kim

  DOI：10.1080/07370650601013179

  日期：2006.12.25
• Synthesis and Photophysical Studies of Heteroleptic Tris-Cyclometalated Ir(III) Complex for Red OLED
  作者：Gui Youn Park、In Joon Kim、Young Sik Kim

  DOI：10.1080/15421400701548316

  日期：2007.9.4