(1-methyl-1H-indol-3-yl) (4-nitrophenyl)methanone

• 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-methyl-1H-indol-3-yl) (4-nitrophenyl)methanone
• 英文别名: (1-methyl-1H-indol-2-yl)(4-nitrophenyl)methanone；(1-methyl-1H-indol-3-yl)(4-nitrophenyl)methanone；1-methyl-1H-indol-3-yl(4-nitrophenyl)methanone；(1-Methylindol-3-yl)-(4-nitrophenyl)methanone
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: OTPZEGYROFYGMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-methyl-1H-indol-3-yl) (4-nitrophenyl)methanone 在 氧气 、 palladium diacetate 、 potassium carbonate 、 三甲基乙酸 作用下， 反应 40.0h， 以69%的产率得到5-Methyl-3-nitroindeno[1,2-b]indol-10-one
  参考文献：
  名称：

  Intramolecular oxidative coupling of 3-indolylarylketones with Pd(II)-catalysis under air: convenient access to indenoindolones

  摘要：

  A Pd-catalyzed method has been developed for the intramolecular oxidative coupling of 3-indolylarylketones under open air as terminal oxidant toward the synthesis of indeno[1,2-b]indol-10(5H)-ones. This reaction represents an intramolecular coupling with dual activation of C-H bonds for electron-deficient arenes, while such reactions are common for electron-rich arenes. Pd(II)-catalysis with pivalic acid as co-catalyst has been found to be crucial. The reaction undergoes without indole N-H-protection. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.076
• 作为产物：
  描述：

  N,N-dimethyl-2-((4-nitrophenyl)ethynyl)aniline 在 叔丁基过氧化氢 、 copper(l) iodide 、 lithium chloride 、 palladium(II) bromide 作用下， 以 癸烷 、 甲苯 为溶剂， 以73%的产率得到(1-methyl-1H-indol-3-yl) (4-nitrophenyl)methanone
  参考文献：
  名称：

  钯-铜-共催化的分子内氧化偶联：合成3-acylindoles的有效和原子经济的策略。

  摘要：

  展示了一种新的高效催化方法，可在Pd-Cu共催化的氧化条件下合成3-acylindoles。叔丁基氢过氧化物（TBHP）在该方法中不仅充当氧化剂，而且充当氧气源。该方法允许从容易获得的原料中快速且原子经济地组装3-acylindoles，并能耐受各种官能团。

  DOI：

  10.1039/c2cc37805a

文献信息

• Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes
  作者：Liquan Yang、Zhaoran Liu、Yujun Li、Ning Lei、Yanling Shen、Ke Zheng

  DOI：10.1021/acs.orglett.9b02433

  日期：2019.10.4

  Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C–N bond cleavage for carbonyl introduction. The key step—the C–N bond cleavage of the Mannich product—was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group

  本文报道的是吲哚与各种醛的氧化交叉偶联的有效策略。该策略基于两步转化，通过众所周知的曼尼希型反应和羰基引入的C–N键裂解实现。关键步骤是曼尼希产品的C–N键断裂—是通过电化学实现的。这种策略（包含40多个示例）可确保出色的官能团耐受性以及药物分子的后期功能化。
• Facile Access to 3-Acylindoles through Palladium-Catalyzed Addition of Indoles to Nitriles: The One-Pot Synthesis of Indenoindolones
  作者：Yuanhong Ma、Jingsong You、Feijie Song

  DOI：10.1002/chem.201203354

  日期：2013.1.21

  The palladium‐catalyzed addition of indoles to nitriles affords 3‐acylindoles. The reaction proceeds with high selectivity, wide substrate scope, broadly available starting materials, and an operationally simple procedure. Combination with the palladium‐catalyzed intramolecular oxidative coupling of 3‐indolylarylketone gives access to indenoindolones in a one‐pot synthesis.

  关联性良好：钯催化的吲哚在腈中的加成反应生成3-acylindoldols。反应以高选择性，广泛的底物范围，广泛可用的起始原料和操作简单的方法进行。与钯催化的3-吲哚基芳基酮的分子内氧化偶合相结合，可在一锅合成中获得茚并吲哚酮。
• Visible light-induced carbonylation of indoles with arylsulfonyl chlorides and CO
  作者：Xiangguang Li、Deqiang Liang、Wenzhong Huang、Hongfu Zhou、Zhao Li、Baoling Wang、Yinhai Ma、Hai Wang

  DOI：10.1016/j.tet.2016.11.009

  日期：2016.12

  A novel and simple strategy for the visible light-induced efficient synthesis of indol-3-yl aryl ketones from readily available arylsulfonyl chlorides and indoles with CO at room temperature was developed. This metal-free protocol has good functional group tolerance and avoids the use of transition-metal catalysts, additives, and alkaline or acidic reaction medium.

  开发了一种新颖，简单的策略，用于在室温下用CO从可见的芳基磺酰氯和吲哚以可见光诱导的吲哚-3-基芳基酮的有效合成。这种不含金属的方案具有良好的官能团耐受性，并且避免使用过渡金属催化剂，添加剂以及碱性或酸性反应介质。
• ZrCl₄-Mediated Regio- and Chemoselective Friedel–Crafts Acylation of Indole
  作者：Sankar K. Guchhait、Maneesh Kashyap、Harshad Kamble

  DOI：10.1021/jo200561f

  日期：2011.6.3

  method for regio- and chemoselective Friedel–Crafts acylation of indole using acyl chlorides in the presence of ZrCl4 has been discovered. It minimizes/eliminates common competing reactions that occur due to high and multiatom-nucleophilic character of indole. In this method, a wide range of aroyl, heteroaroyl alkenoyl, and alkanoyl chlorides undergo smooth acylation with various indoles without NH

  发现了在ZrCl 4存在下使用酰氯对吲哚进行区域选择性和化学选择性Friedel-Crafts酰化的有效方法。它最小化/消除了由于吲哚的高原子和多原子亲核特性而发生的常见竞争反应。在这种方法中，广泛的芳酰基，杂芳基链烯酰基和链烷酰氯与各种没有吲哚保护的吲哚进行平滑的酰化反应，并以高收率或高收率得到了3-酰化吲哚。
• Synthesis of indol-3-yl aryl ketones through visible-light-mediated carbonylation
  作者：Hong-Tao Zhang、Li-Jun Gu、Xiang-Zhong Huang、Rui Wang、Cheng Jin、Gan-Peng Li

  DOI：10.1016/j.cclet.2015.10.012

  日期：2016.2

  Abstract A visible-light-catalyzed synthesis of indol-3-yl aryl ketones from aryldiazonium salts, CO and indoles at room temperature was developed. This process provides a useful method for the preparation of diverse indol-3-yl aryl ketones from readily accessible reactants under base-free, acid-free and transition-metal-free conditions.

  摘要在室温下可见光催化芳基重氮盐，CO和吲哚合成吲哚-3-基芳基酮。该方法提供了一种在无碱，无酸和无过渡金属的条件下由易于获得的反应物制备各种吲哚-3-基芳基酮的有用方法。