4-氯-N-羟基-N-苯基苯甲酰胺 | 29556-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-N-羟基-N-苯基苯甲酰胺
• 英文名称: N-phenyl-p-chlorobenzohydroxamic acid
• 英文别名: 4-Chloro-N-phenylbenzohydroxamic acid；4-chloro-N-hydroxy-N-phenylbenzamide
• CAS: 29556-28-3
• 化学式: C₁₃H₁₀ClNO₂
• 分子量: 247.681
• InChiKey: XTXVIRHMOLMTGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Wilkinson's catalyst 、 4-氯-N-羟基-N-苯基苯甲酰胺 在 Et₃N 作用下， 以 苯 为溶剂， 生成 [Rh(III)(triphenylphosphine)(4-ClC6H4C(O)N(O)C6H5)2Cl]
  参考文献：
  名称：

  异羟肟酸氧化铑（I）。铑（III）双（异羟肟酸酯）配合物的合成，结构和电化学性能。

  摘要：

  There has been considerable interest in the coordination chemistry of the hydroxamic acids (1), because of their relevance in the physiological systems in general and because of their siderophoric activities in microbial transport of iron(3) and their theraputic applications in particular.(4) Hydroxamic acids are known to bind to metal ions usually as a bidentate O,O-donor forming a five-membered chelate ring (2).(5) However, we have recently observed an interesting chemical transformation of N-phenylbenzohydroxamic acids into their corresponding amides, brought about during their reaction with [Os(bPY)(2)Br-2], whereby the amides coordinate to osmium(III) as dianionic C,N-donors (3).(6) This has encouraged us to explore the interaction of the hydroxamic acids with other transition metal ions, preferably in their low oxidation states. For this study we selected rhodium(l) as the low-valent metal ion and N-phenylbenzohydroxamic acids as ligand. It may be mentioned here that though the chemistry of hydroxamate complexes of many transition metals has received considerable attention,(2) that of rhodium, hydroxamates appears to remain completely unexplored. As the source of rhodium(l), the Wilkinson's catalyst, viz. [Rh(PPh3)(3)Cl] was chosen because of its well-known ability to bring about catalytic transformation of organic molecules,7 as well as its efficiency as a synthon. for the preparation of mixed-ligand octahedral complexes of rhodium(III) via oxidative addition of incoming ligands.(8) Reaction of the, N-phenylbenzohydroxamic acids with [Rh(PPh3)(3)Cl] afforded a family of bis(hydroxamate) complexes of rhodium(III) along with the corresponding amides as the byproduct. The chemistry of the bis(hydroxamate) complexes of rhodium(M) is reported here with special reference to their synthesis, structure, and electrochemical properties.

  DOI：

  10.1021/ic0106930
• 作为产物：
  描述：

  硝基苯 在 碳酸氢钠 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 4-氯-N-羟基-N-苯基苯甲酰胺
  参考文献：
  名称：

  Synthesis, crystal structure, spectroscopic properties, DFT calculation and biological activity of 4-chloro-N-(2-(2-nitrophenyl)acetoxy)-N-phenylbenzamide

  摘要：

  4-Chloro-N-(2-(2-nitrophenyl)acetoxy)-N-phenylbenzamide was synthesized and characterized by H-1 NMR, C-13 NMR, MS, IR and X-ray diffraction methods. The structure-property relationship and the antitumor activity based on electrochemical measurements, density functional theory calculations (DFT) and methylthiazolyldiphenyl-tetrazolium bromide (MTT) assay were investigated. The crystal structure adopts monoclinic space group P21/n with the unit cell parameters of a = 12.4385(10) angstrom, b = 6.5036(5) angstrom, c = 24.7944(19) angstrom, beta = 103.045(9)degrees, V = 1954.0(3) angstrom(3), Z = 4, and stabilized by pi-pi conjugation and hydrogen bonding interactions. The observed results of the compound have been compared with theoretical results and it is found that the experimental data show good agreement with calculated values. And the compound had slightly better inhibition than suberoylanilide hydroxamic acid (SAHA) in NCI-H460 cell line as well as the nearly same as SAHA in MCF-7, HCT-116, PC-3, and A549 cell lines. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.08.042

文献信息

• Facile access to amides and hydroxamic acids directly from nitroarenes
  作者：Shreyans K. Jain、K. A. Aravinda Kumar、Sandip B. Bharate、Ram A. Vishwakarma

  DOI：10.1039/c4ob01155d

  日期：——

  for synthesis of amides and hydroxamic acids from nitroarenes and aldehydes is described. The MnO2 catalyzed thermal deoxygenation of nitrobenzene resulted in formation of a reactive nitroso intermediate which on reaction with aldehydes provided amides and hydroxamic acids. The thermal neat reaction in the presence of 0.01 mmol KOH predominantly led to formation of hydroxamic acid whereas reaction

  描述了一种由硝基芳烃和醛合成酰胺和异羟肟酸的新方法。MnO 2催化硝基苯的热脱氧导致形成反应性亚硝基中间体，该中间体在与醛反应后提供酰胺和异羟肟酸。在0.01mmol KOH存在下的热纯反应主要导致异羟肟酸的形成，而在1mmol乙酸存在下的反应产生酰胺作为唯一产物。
• O-Alkyl-N-acyl-N-phenylhydroxylamines as Photochemical Alkoxy Radical Precursors
  作者：Anakuthil Anoop、N. Singh、Nilanjana Chowdhury

  DOI：10.1055/s-0031-1290824

  日期：2012.6

  A simple and efficient technique for the photolysis of alkoxy radical precursors is developed. Irradiation of O-alkyl-N-acyl-N-phenylhydroxylamines, as representative alkoxy radical precursors, with ultraviolet light (≥254 nm) results in homolytic N–O bond cleavage to generate singlet alkoxy and acylaminyl caged radical pairs. These radicals, depending on the solvent employed, either escape from the

  专用于Eluvathongal D. Jemmis教授在他的60之际个生日 抽象 开发了一种简单有效的烷氧基自由基前体的光解技术。用代表性的烷氧基自由基前体辐照O-烷基-N-酰基-N-苯基羟胺（≥254nm）会导致均一的N-O键裂解，从而生成单线烷氧基和酰基丙烯酰胺笼罩的自由基对。这些自由基取决于所使用的溶剂，要么从笼子中逸出以形成片段化产物，要么发生笼中反应以产生光重排产物。使用时变密度泛函理论计算来分析N–O键的均质裂解。所述的性质ñ -酰基取代基上的ø -烷基- Ñ -acyl-N-苯基羟胺显示出影响其产生自由基的能力。此外，证明了烷氧基的识别和捕获。 开发了一种简单有效的烷氧基自由基前体的光解技术。用代表性的烷氧基自由基前体辐照O-烷基-N-酰基-N-苯基羟胺（≥254nm）会导致均一的N-O键裂解，从而生成单线烷氧基和酰基丙烯酰胺笼罩的自由基对。这些自由基取决于所使用的溶剂，要么
• C–H Fluoroalkylsulfinylation/Intramolecular Rearrangement for Precise Synthesis of Fluoroalkyl Sulfoxides
  作者：Shuya Xing、Yu-Yi Zhu、Wen Liu、Yong Liu、Jing Zhang、Huarong Zhang、Yan Wang、Shao-Fei Ni、Xinxin Shao

  DOI：10.1021/acs.orglett.2c01151

  日期：2022.5.13

  ortho/para-functionalized amine scaffolds from arylhydroxylamines is described. The transformation was featured with new electrophilic trifluoromethylthiolated reagents, good functional group tolerance, and late-stage modification of complex bioactive scaffolds, providing a rapid access to prepare numerous trifluoromethyl- and difluoromethyl-substituted sulfoxides. Mechanism studies and density functional

  描述了一种从芳基羟胺中获取各种带有邻位/对位官能化胺支架的氟代烷基亚砜的有效方法。该转化具有新的亲电三氟甲基硫醇化试剂、良好的官能团耐受性和复杂生物活性支架的后期修饰等特点，为制备大量三氟甲基和二氟甲基取代的亚砜提供了快速途径。机理研究和密度泛函理论计算表明，该反应经历了芳基羟胺的亲核三氟甲基硫醇化和随后涉及硫和氧转移过程的内部 2,3-σ 重排。
• Horner; Steppan, Justus Liebigs Annalen der Chemie, 1957, vol. 606, p. 24,36
  作者：Horner、Steppan

  DOI：——

  日期：——
• Choudhuri, S. K.; Roy, P. S.; Ghosh, A. K., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1983, vol. 22, # 11, p. 996 - 998
  作者：Choudhuri, S. K.、Roy, P. S.、Ghosh, A. K.

  DOI：——

  日期：——

表征谱图