4-bromo-N-hydroxy-2-methylbenzamide

• 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: 4-bromo-N-hydroxy-2-methylbenzamide
• 英文别名: 4-Bromo-2-methyl-benzenecarbohydroxamic acid
• 化学式: C₈H₈BrNO₂
• 分子量: 230.061
• InChiKey: JBDFWPJSHYXJQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-N-hydroxy-2-methylbenzamide 、 N-(2-iodophenyl)-N-methyl-3-phenylpropiolamide 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以82%的产率得到(Z)-3-(((4-bromo-2-methylphenyl)amino)(phenyl)methylene)-1-methylindolin-2-one
  参考文献：
  名称：

  钯催化5-exo-dig环化级联反应，用于3-亚甲基吲哚满酮的立体选择性构建的顺序胺化/醚化

  摘要：

  N-（2-碘代苯基）丙酰胺的级联分子内5 -exo-dig环化反应和顺序胺化/醚化（与N-羟基苯甲酰胺，苯基羟基氨基甲酸酯）方案，使用廉价的Pd（已经开发了作为催化剂的PPh 3）4。该协议使具有重要官能团耐受性（特别是卤素基团）的结构重要的羟吲哚核的组装成为可能，从而提供了具有各种取代基的多种产品，收率良好至极佳。

  DOI：

  10.1002/adsc.202001369
• 作为产物：
  描述：

  4-溴-2-甲基苯腈 在 硫酸 、 盐酸羟胺 、 溶剂黄146 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 45.0h， 生成 4-bromo-N-hydroxy-2-methylbenzamide
  参考文献：
  名称：

  Benzohydroxamic acids as potent and selective anti-HCV agents

  摘要：

  A diverse collection of 40 derivatives of benzohydroxamic acid (BHAs) of various structural groups were synthesized and tested against hepatitis C virus (HCV) in full-genome replicon assay. Some of these compounds demonstrated an exceptional activity, suppressing viral replication at sub-micromolar concentrations. The compounds were inactive against key viral enzymes NS3, and NS5B in vitro assays, suggesting host cell inhibition target(s). The testing results were consistent with metal coordination by the BHAs hydroxamic group in complex with a target(s). Remarkably, this class of compounds did not suppress poliomyelitis virus (PV) propagation in RD cells indicating a specific antiviral activity of BHAs against HCV. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.081

文献信息

• Palladium-Catalyzed Cascade Decarboxylative Amination/6-<i>endo-dig</i> Benzannulation of <i>o</i>-Alkynylarylketones with <i>N</i>-Hydroxyamides To Access Diverse 1-Naphthylamine Derivatives
  作者：Youpeng Zuo、Xinwei He、Qiang Tang、Wangcheng Hu、Tongtong Zhou、Yongjia Shang

  DOI：10.1021/acs.orglett.0c01183

  日期：2020.5.15

  An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of

  已经描述了通过连续的钯催化的脱羧胺化/分子内6-endo-dig苯环化反应生产高度取代的1-萘胺的有效且实用的一锅策略。在该反应中，在温和的反应条件下，各种各样的富电子，电子中性和缺电子的邻炔基芳基酮都能与N-羟基芳基/烷基酰胺良好反应，从而以优异的产率获得各种1-萘胺。克级合成法具有诸如不降低产品收率和易于转化的优点，说明了该方法的实用性。
• Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones
  作者：Taibei Fang、Shiwen Zhang、Qingqing Ye、Shuwen Kong、Tingting Yang、Kaijie Tang、Xinwei He、Yongjia Shang

  DOI：10.3390/molecules27238553

  日期：——

  A sequential Rh(III)-catalyzed C-H activation/annulation of N-hydroxybenzamides with propargylic acetates leading to the formation of NH-free isoquinolones is described. This reaction proceeds through a sequential C-H activation/alkyne insertion/intramolecular annulation/N-O bond cleavage procedure, affording a broad spectrum of products with diverse substituents in moderate-to-excellent yields. Notably

  描述了 N-羟基苯甲酰胺与炔丙基乙酸酯的顺序 Rh (III) 催化的 CH 活化/环化，导致形成不含 NH 的异喹诺酮。该反应通过连续的 CH 活化/炔烃插入/分子内环化/NO 键裂解过程进行，以中等到极好的收率提供具有不同取代基的广泛产物。值得注意的是，该协议的特点是在一个锅中同时形成两个新的 CC/CN 键和一个杂环，同时释放水作为唯一的副产品。
• Ir(<scp>iii</scp>)/Ag(<scp>i</scp>)-catalyzed directly C–H amidation of arenes with OH-free hydroxyamides as amidating agents
  作者：Youpeng Zuo、Meijun Liu、Jun Du、Tianren Zhang、Xiaoqing Wang、Cong Wang

  DOI：10.1039/d4ra00517a

  日期：——

  A versatile Ir(III)-catalyzed C–H amidation of arenes by employing readily available and stable OH-free hydroxyamides as a novel amidation source. The reaction occurred with high efficiency and tolerance of a range of functional groups. A wide scope of aryl OH-free hydroxyzamides, including conjugated and challenging non-conjugated OH-free hydroxyzamides, were capable of this transformation and no

  采用易得且稳定的不含 OH 的羟基酰胺作为新型酰胺化源，实现了多功能 Ir( III ) 催化的芳烃 C-H 酰胺化。该反应以高效率发生并且对一系列官能团具有耐受性。多种不含芳基 OH 的羟基酰胺，包括共轭和具有挑战性的非共轭不含 OH 的羟基酰胺，都能够进行这种转化，并且无需添加外部氧化剂。该方案为多种N -(2-(1 H-吡唑-1-基)烷基)酰胺衍生物提供了一种简单、直接且经济的方法，具有良好的收率。机理研究表明可逆的C-H键功能化可能参与该反应。
• Benzohydroxamic acids as potent and selective anti-HCV agents
  作者：Maxim V. Kozlov、Alla A. Kleymenova、Lyudmila I. Romanova、Konstantin A. Konduktorov、Olga A. Smirnova、Vladimir S. Prasolov、Sergey N. Kochetkov

  DOI：10.1016/j.bmcl.2013.08.081

  日期：2013.11

  A diverse collection of 40 derivatives of benzohydroxamic acid (BHAs) of various structural groups were synthesized and tested against hepatitis C virus (HCV) in full-genome replicon assay. Some of these compounds demonstrated an exceptional activity, suppressing viral replication at sub-micromolar concentrations. The compounds were inactive against key viral enzymes NS3, and NS5B in vitro assays, suggesting host cell inhibition target(s). The testing results were consistent with metal coordination by the BHAs hydroxamic group in complex with a target(s). Remarkably, this class of compounds did not suppress poliomyelitis virus (PV) propagation in RD cells indicating a specific antiviral activity of BHAs against HCV. (C) 2013 Elsevier Ltd. All rights reserved.
• Palladium‐Catalyzed 5‐ <i>exo‐dig</i> Cyclization Cascade, Sequential Amination/Etherification for Stereoselective Construction of 3‐Methyleneindolinones
  作者：Youpeng Zuo、Xinwei He、Qiang Tang、Wangcheng Hu、Tongtong Zhou、Wenbo Hu、Yongjia Shang

  DOI：10.1002/adsc.202001369

  日期：2021.4.13

  An cascade intramolecular 5‐exo‐dig cyclization of N‐(2‐iodophenyl)propiolamides and sequential amination/etherification (with N‐hydroxybenzamides, phenyl hydroxycarbamate) protocol for the synthesis of amino‐ and phenoxy‐substituted 3‐methyleneindolinones using unexpensive Pd(PPh3)4 as catalyst has been developed. The protocol enables the assembly of structurally important oxindole cores featuring

  N-（2-碘代苯基）丙酰胺的级联分子内5 -exo-dig环化反应和顺序胺化/醚化（与N-羟基苯甲酰胺，苯基羟基氨基甲酸酯）方案，使用廉价的Pd（已经开发了作为催化剂的PPh 3）4。该协议使具有重要官能团耐受性（特别是卤素基团）的结构重要的羟吲哚核的组装成为可能，从而提供了具有各种取代基的多种产品，收率良好至极佳。