2-amino-5-chloro-N-hydroxybenzamide | 84712-07-2

• 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: 2-amino-5-chloro-N-hydroxybenzamide
• CAS: 84712-07-2
• 化学式: C₇H₇ClN₂O₂
• mdl: MFCD09901787
• 分子量: 186.598
• InChiKey: QXWGUYFUOSHVHY-UHFFFAOYSA-N

物化性质

• 熔点：
  148-149 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-chloro-N-hydroxybenzamide 以 formamide 为溶剂， 反应 0.33h， 以94.2%的产率得到5-氯-1,3-二氢苯并咪唑-2-酮
  参考文献：
  名称：

  通过修饰的Lossen重排轻松合成苯并咪唑-2-酮衍生物

  摘要：

  DOI：

  10.1021/je00032a042
• 作为产物：
  描述：

  2-氨基-5-氯苯甲酸甲酯 在 ammonium hydroxide 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 2-amino-5-chloro-N-hydroxybenzamide
  参考文献：
  名称：

  Tandem C–O and C–N Bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Salts: Synthesis of N-Aryl Benzo[1,2,3]triazin-4(1H)-one Derivatives

  摘要：

  Metal-free O-arylation and [3, 3]-rearrangement have been shown as an efficient strategy to construct new C-O and C-N bonds in one-pot reactions. The method was used to prepare N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one and diaryliodonium salts. The reaction was tolerated a variety of sensitive functional groups such as iodine, nitro, ester, and aldehyde groups. A rational mechanism was proposed based on the experimental results, and the reaction was easily up to gram scale.

  DOI：

  10.1021/acs.joc.5b01947

文献信息

• Parallel synthesis and in vitro activity of novel anthranilic hydroxamate-based inhibitors of the prostaglandin H2 synthase peroxidase activity
  作者：Jean Lee、Anthony J. Chubb、Edelmiro Moman、Brian M. McLoughlin、Caroline T. Sharkey、John G. Kelly、Kevin B. Nolan、Marc Devocelle、Desmond J. Fitzgerald

  DOI：10.1039/b505525c

  日期：——

  Currently available non-steroidal anti-inflammatory drugs (NSAIDs) such as aspirin are directed at the cyclooxygenase (COX) site, but not the peroxidase (POX) activity of prostaglandin H2 synthase (PGHS). They are thus unable to inhibit the free-radical induced tissue injury associated with PGHS peroxidase activity, which can occur independently of the COX site. A lead compound, anthranilic hydroxamic

  当前可用的非甾体抗炎药（NSAID）（例如阿司匹林）针对的是环氧合酶（COX）位点，而不针对前列腺素H2合酶（PGHS）的过氧化物酶（POX）活性。因此，它们不能抑制与PGHS过氧化物酶活性相关的自由基诱导的组织损伤，而损伤可能独立于COX部位而发生。发现先导化合物邻氨基苯甲酸异羟肟酸（AHA）具有显着的PGHS-POX抑制活性（IC50 = 72 microM）。为了定义抑制PGHS-POX的关键参数，我们研究了使用固相合成方法从其酸前体合成的29种AHA衍生物。体外分析表明3,5-二碘邻氨基苯甲酸异羟肟酸（IC50 = 7 microM）的抑制作用提高了十倍。
• Synthesis and Application of<i>N</i>-Hydroxylamine Derivatives as Potential Replacements for HOBt
  作者：Ayman El-Faham、Fernando Albericio

  DOI：10.1002/ejoc.200801179

  日期：2009.4

  [a] Institute for Research in Biomedicine,Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona,SpainE-mail: [e-mail][b] Department of Chemistry, Faculty of Science, Alexandria Uni-versity,Ibrahimia 21321, Alexandria, EgyptE-mail: [e-mail][c] Department of Chemistry, College of Science, King Saud Uni-versity,P. O. Box 2455, Riyadh, Saudi Arabia[d] Department of

  [a] 生物医学研究所，Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona,​​SpainE-mail: [e-mail][b] 亚历山大大学理学院化学系，Ibrahimia 21321，亚历山大，埃及电子邮件：[e-mail][c] 沙特国王大学理学院化学系，邮政信箱 2455，利雅得，沙特阿拉伯[d] 巴塞罗那大学有机化学系，Marti i Franques 1 -11, 08028 Barcelona,​​ Spain[e] CIBER-BBN，生物工程、生物材料和纳米医学网络中心，巴塞罗那科学园，Baldiri Reixac 10, 08028 Barcelona,​​ Spain本文的支持信息可在 WWW 上获得，网址为 http:// www.eurjoc
• PROTON ACCEPTOR IMINIUM/CARBOCATION-TYPE COUPLING AGENTS
  申请人：Albericio Fernando

  公开号：US20100144588A1

  公开（公告）日：2010-06-10

  Novel iminium-type coupling agents containing proton acceptors in their iminium moiety, which can be used beneficially as coupling agents in various chemical polypeptide and/or polynucleotide syntheses, and are particularly useful as yield enhancing and racemization suppressing coupling agents for use in peptide syntheses, are disclosed. Further disclosed are a process of preparing such iminium-type coupling agents and their use in the preparation of polypeptides and/or polynucleotides.

  包含质子受体的新型亚胺型偶联剂，可有益地用作各种化学多肽和/或多核苷酸合成中的偶联剂，并且特别适用于在肽合成中提高产率和抑制旋光异构化的偶联剂。还公开了一种制备这种亚胺型偶联剂的方法以及它们在多肽和/或多核苷酸制备中的用途。
• Bifunctional Phosphine Ligand-Enabled Gold(I)-Catalyzed O-Nucleophilic Addition of <i>N</i>-Hydroxybenzo[1,2,3]-triazin-4(3<i>H</i>)-ones to Alkynes Followed by [3,3]-Rearrangement: Simultaneous Formation of C–O and C–N Bonds
  作者：Yongcai Xu、Kanghe Zheng、Bingwei Zhou、Hongwei Jin、Yunkui Liu

  DOI：10.1021/acs.joc.0c00471

  日期：2020.5.15

  We describe a gold (I)-catalyzed tandem O-nucleophilic addition/[3,3]-rearrangement reaction of N-hydroxybenzo[1,2,3]-triazin-4(3H)-ones with alkynes enabled by a biphenyl-2-yl phosphine ligand featuring a pendant amide moiety (L1). A variety of 1-(2-oxo-2-arylethyl)benzo [d][1,2,3]triazin-4(1H)-one derivatives were synthesized in good to excellent yields. The present protocol gives a rare example

  我们描述了金（I）催化串联N-羟基苯并[1,2,3] -triazin-4（3H）-ones与炔烃通过联苯-启用的串联O-亲核加成/ [3,3]-重排反应。具有酰胺侧基（L1）的2-基膦配体。合成了多种1-（2-氧代-2-芳基乙基）苯并[d] [1,2,3]三嗪-4（1H）-一衍生物，其收率高至优异。本协议给出了一个罕见的例子，在金（I）催化的[3,3]-σ重排中同时形成CO和CN键。
• Compositions containing N-amino- and N-hydroxy-quinazolinones and methods for preparing libraries thereof
  申请人：——

  公开号：US20010018518A1

  公开（公告）日：2001-08-30

  The present invention is directed to certain N-amino- and N-hydroxy-quinazolinone compounds and synthetic methods for synthesis thereof, which compounds may find use in combinatorial libraries. More specifically, the invention is directed to the synthesis of 3-hydroxy- and 3-amino-4(1H)-quinazolinones via the reaction of an appropriate 2-aminobenzamide compound with a carboxylic acid or acyl halide at ambient temperature performed on a solid support or in solution.

  本发明涉及某些N-氨基和N-羟基喹唑酮化合物及其合成方法，这些化合物可在组合化学库中找到应用。更具体地，本发明涉及通过在固体支持物或溶液中在环境温度下将适当的2-氨基苯甲酰胺化合物与羧酸或酰卤反应来合成3-羟基和3-氨基-4（1H）-喹唑酮的合成方法。