1-acetyl-2-(3,4-dimethoxyphenyl)-2,3-dihydro-1H-indole | 823791-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-acetyl-2-(3,4-dimethoxyphenyl)-2,3-dihydro-1H-indole
• 英文别名: 1-[2-(3,4-Dimethoxyphenyl)-2,3-dihydro-1H-indol-1-yl]ethan-1-one；1-[2-(3,4-dimethoxyphenyl)-2,3-dihydroindol-1-yl]ethanone
• CAS: 823791-71-5
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: URJXZPJAKLLYII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘乙酰苯胺 在 palladium diacetate 、 三氯化铁 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-acetyl-2-(3,4-dimethoxyphenyl)-2,3-dihydro-1H-indole
  参考文献：
  名称：

  A tandem highly stereoselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction

  摘要：

  dA conceptually distinctive stereoselective construction of the novel dimer, N-[N'-acetyl-7,7'-bis-(3,4-dimethoxy-phenyl)-7,8,7',8'-tetrahydro-N'H-[8,8']biindolyl-N-yl]-ethanone 25 (bisindoline) is described below. These structures, which include 7-(3,4-dimethoxyphenyl)-indoline 24 (veratryl indoline), were obtained by the tactical combination of palladium-catalysed coupling which produced 10-acetamido-3,4-dimethoxystilbene 9, followed by FeCl3 induced oxidative cyclization/dimerization. All new structures were fully characterized by 1- and 2D NMR spectroscopy, (proton, carbon-13, COSY, HMBC, HMQC) and mass spectrometry. Configurational assignments were further supported by semi-empirical AMI calculations. Mechanistic interpretations, consistent with our results, are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.002

文献信息

• Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles
  作者：Naoki Morimoto、Kumika Morioku、Hideyuki Suzuki、Yasuo Takeuchi、Yuta Nishina

  DOI：10.1021/acs.orglett.6b00629

  日期：2016.5.6

  been functionalized using this property. Indole also forms indolium, which allows electrophilic addition in acidic conditions, but current examples have been limited to intramolecular reactions. C2 site-selective nucleophilic addition to indole derivatives using fluoroalcohol and a Lewis acid was developed.

  吲哚很容易在C3位发生亲核取代，许多吲哚衍生物已利用此特性进行了功能化。吲哚还形成吲哚，允许在酸性条件下进行亲电加成，但目前的例子仅限于分子内反应。开发了使用氟代醇和路易斯酸对吲哚衍生物进行C2位点选择性亲核加成反应。
• Electrochemically Mediated Oxidative Transformations of Substituted 4-Methoxystilbenes: Effect of Ortho-Substituted Nucleophilic Groups
  作者：Kam-Weng Chong、Fong-Jiao Hong、Noel F. Thomas、Yun-Yee Low、Toh-Seok Kam

  DOI：10.1021/acs.joc.7b00753

  日期：2017.6.16

  undertaken to determine the influence of ortho′-substituted nucleophilic groups (OH, NH2, or NHR) on the reactivity of anodically generated 4-methoxy- and 3,4-dimethoxystilbene cation radicals. The results showed that when ortho-substituted nucleophilic groups such as OH and NHR are present in the other ring, both direct and crossover intramolecular cation–nucleophile reactions occur to give bisbenzofurans/bisindoles

  进行了系统的研究，以确定邻位取代的亲核基团（OH，NH 2（或NHR）对阳极产生的4-甲氧基和3,4-二甲氧基苯乙烯阳离子自由基的反应性。结果表明，当另一个环上存在邻位取代的亲核基团（例如OH和NHR）时，分子内直接和交叉的阳离子-亲核反应都会分别产生双苯并呋喃/双吲哚或稠合的双苯并吡喃/双喹啉。当存在另外的3-甲氧基取代基时，除了双苯并吡喃/双喹啉和双苯并呋喃/双吲哚之外，还形成桥连的氧代辛/偶氮产物。基于观察到的行为的机械合理化，该过程基于涉及电子转移后快速阳离子自由基二聚化的广义路径，然后通过邻位取代的氧和氮亲核基团直接和交叉捕获苄基阳离子。在存在额外的3-甲氧基的情况下，由于竞争性芳族取代（Friedel-Crafts反应），还形成了桥接的氧代辛/偶氮产物。结果提供了进一步的启示，并进一步澄清了阳极产生的二苯乙烯阳离子自由基的反应性。
• The Subtle Co-catalytic Intervention of Benzophenone in Radical Cation Mediated Cyclization — An Improved Synthesis of 2-(3’,4’-Dimethoxyphenyl)indoline
  作者：Noel Francis Thomas、Chin-Hui Kee、Azhar Ariffin、Khalijah Awang、Jean-Fr仕屍ic Faizal Weber、Chuan-Gee Lim、Mat Ropi Mukhtar、A. Hamid A. Hadi

  DOI：10.3987/com-07-11280

  日期：——

  The addition of benzophenone to a FeCl 3 /CH 2 Cl 2 mixture in the presence of 3',4'-dimethoxy-2-acetamidostilbene 17 unexpectedly leads to a dramatic improvement in yield of the indoline 20 from 38% (previously reported by us) to 75.4%, after careful examination of a variety of reaction conditions. A catalytic cycle has been proposed that involves not only stilbene radical cations but also Fe 2+ promoted

  在 3',4'-dimethoxy-2-acetamidostilbene 17 存在下，将二苯甲酮添加到 FeCl 3 /CH 2 Cl 2 混合物中意外地导致二氢吲哚 20 的产率从 38% 显着提高（我们之前报道过） ) 至 75.4%，经过仔细检查各种反应条件。已经提出了一种催化循环，该循环不仅涉及二苯乙烯自由基阳离子，而且还包括促进二苯甲酮酮基自由基形成的 Fe 2+ ，这增强了环化作用，抑制了二聚化，并解释了二苯甲酮的几乎定量回收。
• A tandem highly stereoselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction
  作者：Noel F. Thomas、Saraswati S. Velu、Jean-Frédéric F. Weber、K.C. Lee、A. Hamid A. Hadi、Pascal Richomme、David Rondeau、Ibrahim Noorbatcha、Khalijah Awang

  DOI：10.1016/j.tet.2004.10.002

  日期：2004.12

  dA conceptually distinctive stereoselective construction of the novel dimer, N-[N'-acetyl-7,7'-bis-(3,4-dimethoxy-phenyl)-7,8,7',8'-tetrahydro-N'H-[8,8']biindolyl-N-yl]-ethanone 25 (bisindoline) is described below. These structures, which include 7-(3,4-dimethoxyphenyl)-indoline 24 (veratryl indoline), were obtained by the tactical combination of palladium-catalysed coupling which produced 10-acetamido-3,4-dimethoxystilbene 9, followed by FeCl3 induced oxidative cyclization/dimerization. All new structures were fully characterized by 1- and 2D NMR spectroscopy, (proton, carbon-13, COSY, HMBC, HMQC) and mass spectrometry. Configurational assignments were further supported by semi-empirical AMI calculations. Mechanistic interpretations, consistent with our results, are discussed. (C) 2004 Elsevier Ltd. All rights reserved.