2,4-dichlorobenzohydroxamic acid | 2593-23-9

• 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: 2,4-dichlorobenzohydroxamic acid
• 英文别名: 2,4-dichloro-N-hydroxybenzamide；2,4-dichloro-N-hydroxy-benzamide；2,4-Dichlor-benzhydroxamsaeure
• CAS: 2593-23-9
• 化学式: C₇H₅Cl₂NO₂
• mdl: MFCD04067569
• 分子量: 206.028
• InChiKey: ZHHUWPHSXFCRIP-UHFFFAOYSA-N

物化性质

• 熔点：
  155 °C
• 密度：
  1.529±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2,4-dichlorobenzohydroxamic acid 在 三乙胺 、 iron(II) chloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 22.0h， 生成 2,4-dichloro-N-(triphenyl-l5-phosphaneylidene)benzamide
  参考文献：
  名称：

  铁(II)催化膦与N-酰氧基酰胺的亚胺化构建N-酰基亚氨基正膦

  摘要：

  使用 FeCl 2作为廉价且容易获得的催化剂，描述了膦与 N-酰氧基酰胺的简便亚胺化反应，提供了具有高官能团耐受性的合成有用的N-酰基亚氨基正膦。该转化在室温下的空气气氛下很容易进行，并且可以在催化剂负载量为 1 mol% 的情况下放大至克级。产物中的亚氨基正膦基部分被进一步用作在 Rh(III) 催化下可控邻位C(sp 2 )-H 键酰胺化的有效导向基团。

  DOI：

  10.1021/acs.orglett.2c01238
• 作为产物：
  描述：

  2,4-二氯苯甲酸 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 20.5h， 以60%的产率得到2,4-dichlorobenzohydroxamic acid
  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

• A convenient parallel synthesis of low molecular weight hydroxamic acids using polymer-supported 1-hydroxybenzotriazole
  作者：Marc Devocelle、Brian M. McLoughlin、Caroline T. Sharkey、Desmond J. Fitzgerald、Kevin B. Nolan

  DOI：10.1039/b211526c

  日期：2003.2.27

  parallel synthesis of hydroxamic acids from carboxylic acids and hydroxylamine in good to high yields is reported. It involves the formation of a polymer-bound HOBt active ester and subsequent reaction with O-protected or free hydroxylamine. The hydroxamates are isolated with high purities by simple evaporation of volatile solvents. The use of free hydroxylamine leads to increased yields while maintaining

  报道了一种方便的两步法，可以从羧酸和羟胺以高产率到高产率并行合成异羟肟酸。它涉及形成聚合物结合的HOBt活性酯，然后与O保护的或游离的羟胺反应。通过简单蒸发挥发性溶剂可以高纯度分离出异羟肟酸酯。游离羟胺的使用可提高产量，同时保持高纯度。废树脂的再循环以生产相同或不同的异羟肟酸已通过三步协议完成，该协议易于实现自动化且经济实惠。本文介绍的方法非常适合标题化合物的制备，可有效地用于合成含有异羟肟酸基团的大分子。
• New Coordination Modes of Substituted Benzohydroxamic Acid with Dialkyltin(IV): Structural Diversity through Ligand Isomerization
  作者：Xian‐mei Shang、Ji‐zhou Wu、Qing‐shan Li

  DOI：10.1002/ejic.200600546

  日期：2006.10

  complexes were characterized by elemental analysis, IR, 1H, 13C, 119Sn NMR spectra and X-ray diffraction analysis. The results indicated overall (Z)-iminol coordination mode in the hydroximic tautomeric form for 1 and 2, and keto-iminol mixed-coordination mode including both in (Z)-hydroxamic and -hydroximic tautomeric forms for 3 and 4. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  当R2SnCl2（R=Me，nBu）与取代苯异羟肟酸（取代基=4-F；2,4-Cl2；2,5-F2）和氢氧化钾在甲醇水溶液中反应时，可以得到两种缩合产物，取决于摩尔比 R2SnCl2/RCONHOH/KOH。当使用 1:1:2 摩尔比时，1:1 烷基锡异羟肟酸盐 (n-C4H9)2Sn[4-FC6H4C(O)NO]}n (1) 和 (CH3)2Sn[2,5-F2C6H3C (O)NO]}n (2) 形成。当使用 1:2:2 比例时，另外两种意想不到的 2:3 异羟肟酸烷基锡，( )4Sn2[(2,4-Cl2C6H3C(O)NHO)2][2,4-Cl2C6H3C(O)NO]得到}n (3) 和 (n- )4Sn2[(4-FC6H4C(O)NHO)2][4-FC6H4C(O)NO]}n(4)。所有这些配合物均通过元素分析、IR、1H、13C、119Sn NMR 光谱和 X 射线衍射分析进行表征。结果表明
• Iron(II)-Catalyzed Nitrene Transfer Reaction of Sulfoxides with <i>N</i>-Acyloxyamides
  作者：Tianxing Qi、Ning Fang、Weimin Huang、Jianhui Chen、Yanshu Luo、Yuanzhi Xia

  DOI：10.1021/acs.orglett.2c01990

  日期：2022.8.12

  An iron(II)-catalyzed nitrene transfer reaction of sulfoxides with N-acyloxyamides has been developed, leading to the efficient construction of N-acyl sulfoximines with high functional-group compatibility. The current catalytic transformation was carried out under an air atmosphere at ambient temperature and could be scaled up to gram scale with a catalyst loading of 1 mol %. Application of the methodology

  已经开发了亚砜与 N-酰氧基酰胺的铁 (II) 催化的氮烯转移反应，从而有效地构建了具有高官能团相容性的N-酰基亚砜亚胺。目前的催化转化是在环境温度下的空气气氛下进行的，并且可以在催化剂负载量为 1 mol% 的情况下放大至克级。该方法的应用通过使用N-酰基亚砜亚胺作为导向基团的简单 C-H 乙酰氧基化和烯化来证明。
• 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。
• Condition-Controlled <i>O</i>-Acylation and N–O Bond Reduction of Hydroximic Acids with Thioacetic Acid
  作者：Risong Wang、Yifei Chen、Binjie Fei、Jiahao Hu、Jianhui Chen、Yanshu Luo、Yuanzhi Xia

  DOI：10.1021/acs.orglett.3c00735

  日期：2023.5.5

  Condition-dependent transformations between hydroximic acids and thioacetic acid were achieved. Using NH4HCO3 in the ethanol solvent, efficient N–O bond cleavage of hydroxamic acids occurred to afford primary amides with high functional group compatibility. The reaction was switched to O-acylation when NEt3 and H2O were used as the base and solvent, respectively. These facile transformations could

  实现了羟肟酸和硫代乙酸之间的条件依赖性转化。在乙醇溶剂中使用 NH 4 HCO 3，异羟肟酸发生有效的 N-O 键断裂，得到具有高官能团相容性的伯酰胺。当NEt 3和H 2 O分别用作碱和溶剂时，反应切换到O-酰化。这些简单的转换可以顺利地放大到克级。初步的机理研究表明，N-O 键断裂涉及酰化/还原的级联过程。