1-(4-fluorophenyl)-2-phenyl-1H-indole

• 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: 1-(4-fluorophenyl)-2-phenyl-1H-indole
• 英文别名: 1-(4-Fluorophenyl)-2-phenylindole
• 化学式: C₂₀H₁₄FN
• 分子量: 287.336
• InChiKey: ADQAYSIPGROGMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 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：
  4.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-2-phenyl-1H-indole 、 1-((N,4-dimethylphenyl)sulfonamido)pyridin-1-ium tetrafluoroborate 以 乙腈 为溶剂， 以86 %的产率得到N-(1-(4-fluorophenyl)-2-phenyl-1H-indol-3-yl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  电子供体-受体复合物引发的吲哚的可见光驱动无催化剂胺化

  摘要：

  在没有任何添加剂的情况下，可见光驱动的吲哚 C2 或 C3 胺化是通过由吲哚和N-氨基吡啶盐形成的电子供体-受体 (EDA) 复合物引发的。该方法与多种底物兼容，无需添加任何光催化剂、过渡金属催化剂或碱即可顺利进行。进行了各种研究以检查 EDA 复合物的存在。

  DOI：

  10.1002/cjoc.202200772
• 作为产物：
  描述：

  1-氯-2-碘苯 在 palladium diacetate copper(l) iodide 、 potassium tert-butylate 、 caesium carbonate 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 甲苯 为溶剂， 反应 35.0h， 生成 1-(4-fluorophenyl)-2-phenyl-1H-indole
  参考文献：
  名称：

  Three-component indole synthesis using ortho-dihaloarenes

  摘要：

  A three-component synthesis of substituted indoles is accomplished starting from ortho-dihaloarenes through the use of a multicatalytic system consisting of an N-heterocyclic carbene palladium complex and CuI. The corresponding indole derivatives are obtained as single regioisomers in high yields of isolated product. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.095

文献信息

• A Highly Selective Tandem Cross-Coupling of <i>gem</i>-Dihaloolefins for a Modular, Efficient Synthesis of Highly Functionalized Indoles
  作者：Yuan-Qing Fang、Mark Lautens

  DOI：10.1021/jo701987r

  日期：2008.1.1

  A highly efficient method of indole synthesis using gem-dihalovinylaniline substrates and an organoboron reagent was developed via a Pd-catalyzed tandem intramolecular amination and an intermolecular Suzuki coupling. Aryl, alkenyl, and alkyl boron reagents are all successfully employed, making for a versatile modular approach. The reaction tolerates a variety of substitution patterns on the aniline

  使用吲哚合成法的高效率的方法偕- dihalovinylaniline底物和有机硼试剂经由Pd催化的分子内串联胺化和分子间Suzuki偶联显影。芳基，烯基和烷基硼试剂均已成功使用，从而形成了一种通用的模块化方法。该反应耐受苯胺上的多种取代方式，从而导致吲哚类化合物的基团在C 2 -C 7处。铜和钯介导的1,2-二芳基吲哚顺序合成的正交方法开发了多种有机硼试剂的广泛应用。
• Selective arylation/annulation cascade reactions of 2-alkynylanilines with diaryliodonium salts
  作者：Ying Duan、Yanliang Yang、Xiaoyu Dai、Dongmi Li

  DOI：10.1016/s1872-2067(16)62522-6

  日期：2016.11

  Abstract An efficient Cu catalyzed selective arylation/annulation cascade reaction of 2-alkynylanilines with diaryliodonium salts was developed. This reaction was selective to N-arylation instead of C-arylation, which provides a simple synthetic method for N-aryl indoles.

  摘要 开发了一种有效的 Cu 催化的 2-炔基苯胺与二芳基碘鎓盐的选择性芳基化/环化级联反应。该反应对N-芳基化而不是C-芳基化具有选择性，为N-芳基吲哚提供了一种简单的合成方法。
• Exploration of C–H and N–H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines
  作者：Michael Ghobrial、Marko D Mihovilovic、Michael Schnürch

  DOI：10.3762/bjoc.10.226

  日期：——

  The synthesis of 1,2,3-trisubstituted indoles was investigated. More specifically, straightforward synthetic routes towards 1-(1,2-diarylindol-3-yl)-N-PG-THIQs (PG = protecting group, THIQ = tetrahydroisoquinoline) employing transition metal-catalyzed C–H and N–H-bond functionalization were explored. It was found that the synthesis of the target compounds is strongly dependent on the order of events. Hence, depending on the requirements of a synthetic problem the most suitable and promising pathway can be chosen. Additionally, a new synthetic approach towards 1,2-diarylindoles starting from 1-arylindole could be established in the course of our investigation by using a palladium-catalyzed protocol. Such 1,2-diarylindoles were successfully reacted with N-Boc-THIQ to furnish 1,2,3-trisubstituted indoles as target compounds. Furthermore, regioselective N-arylation of protected and unprotected 1-(indol-3-yl)-THIQs was successfully conducted using either simple iron or copper salts as catalysts.

  对1,2,3-三取代吲哚的合成进行了研究。更具体地，探索了通过过渡金属催化的C-H和N-H键官能化的直接合成途径，以制备1-(1,2-二芳基吲哚-3-基)-N-PG-THIQs（PG = 保护基，THIQ = 四氢异喹啉）。发现目标化合物的合成强烈依赖于事件的顺序。因此，根据合成问题的要求，可以选择最合适和最有前途的途径。此外，在我们的研究过程中，通过使用钯催化的方法，建立了从1-芳基吲哚出发合成1,2-二芳基吲哚的新合成方法。这种1,2-二芳基吲哚成功地与N-Boc-THIQ反应，生成1,2,3-三取代吲哚作为目标化合物。此外，使用简单的铁盐或铜盐作为催化剂，成功地对受保护和未受保护的1-(吲哚-3-基)-THIQ进行了区域选择性N-芳基化反应。
• Transition-Metal-Free Synthesis of 1,2-Disubstituted Indoles
  作者：Gleb A. Chesnokov、Alexandra A. Ageshina、Maxim A. Topchiy、Mikhail S. Nechaev、Andrey F. Asachenko

  DOI：10.1002/ejoc.201900772

  日期：2019.8.15

  A new robust transition‐metal‐free method for synthesis of 1,2‐disubstituted indoles from easily available tertiary amides is presented. This approach can be performed in a one‐pot two‐step manner directly from secondary amines. Mechanistic studies showed that acyl transfer might be an important step in the course of the reaction. Viability of the presented approach for benzofurans and benzothiophenes

  提出了一种新的耐用的无过渡金属的方法，由易于获得的叔酰胺合成1,2-二取代的吲哚。该方法可以直接从仲胺以一锅两步的方式进行。机理研究表明，酰基转移可能是反应过程中的重要一步。还证明了所提出的方法对于苯并呋喃和苯并噻吩合成的可行性。
• Access to Indole Derivatives from Diaryliodonium Salts and 2-Alkynylanilines
  作者：Pengfei Li、Yunxiang Weng、Xianxiang Xu、Xiuling Cui

  DOI：10.1021/acs.joc.6b00106

  日期：2016.5.20

  2-disubstituted indoles from 2-alkynylanilines and diaryliodonium salts has been developed. This reaction proceeds smoothly under metal-free conditions. The products obtained could be transferred into 3,3′-diindolylmethane with DMSO catalyzed by palladium. The isotopic label experiments indicated that the methylene group in 3,3′-diindolylmethane is derived from DMSO. The diverse indoles were obtained

  已经开发了一种从2-炔基苯胺和二芳基碘鎓盐制备1，2-二取代的吲哚的有效，环保且操作简单的方法。该反应在无金属的条件下顺利进行。得到的产物可以用钯催化的DMSO转移到3，3′-二吲哚基甲烷中。同位素标记实验表明3,3'-二吲哚基甲烷中的亚甲基衍生自DMSO。对于28个实例，以高达90％的产率获得了多种吲哚。