3-氟-N-(4-甲基苯基)苯甲酰胺 | 398-80-1

• 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: 3-氟-N-(4-甲基苯基)苯甲酰胺
• 英文名称: 3-fluoro-N-(p-tolyl)benzamide
• 英文别名: 3-fluoro-N-(4-methylphenyl)benzamide
• CAS: 398-80-1
• 化学式: C₁₄H₁₂FNO
• 分子量: 229.254
• InChiKey: YGYASICDDPBVIN-UHFFFAOYSA-N

物化性质

• 沸点：
  275.8±33.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

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：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氟苯腈 、 bis(4-methylphenyl)iodonium trifluoromethanesulfonate 在 水 、 copper diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 以57%的产率得到3-氟-N-(4-甲基苯基)苯甲酰胺
  参考文献：
  名称：

  使用腈作为酰胺化试剂的无配体铜催化的二芳基碘鎓盐的直接酰胺化

  摘要：

  通过铜催化的二芳基碘鎓盐与腈的酰胺化反应，已经开发出一种有效且实用 的合成N-芳基酰胺的方法。可以在反应中应用各种取代的芳基腈和脂族腈，以中等至良好的产率提供一系列的N-芳基化酰胺。该程序为合成各种N-芳基酰胺提供了另一种途径。还提出了一种基于控制实验的机制。

  DOI：

  10.1016/j.tetlet.2021.153048

文献信息

• 一种N-芳基酰胺类化合物的制备方法
  申请人：广东石油化工学院

  公开号：CN111302967A

  公开（公告）日：2020-06-19

  本发明公开了一种N‑芳基酰胺类化合物的制备方法，包括如下步骤：（1）在配有磁力搅拌棒的Schlenk管中，装入二芳基碘鎓盐和Cu（OAc）2；（2）用注射器依次添加DCE、H2O和腈，将Schlenk管密封80℃搅拌反应；（3）将所得溶液冷却至室温，并用EtOAc萃取；合并有机层用盐水洗涤，并用无水Na2SO4干燥；（4）真空除去挥发物，残余物通过柱色谱法纯化得到N‑芳基酰胺类化合物。本发明经过大量实验，筛选了结构简单的底物，并且其反应条件温和、产率高、污染小，应用前景广阔。
• Synthesis of Anilides by Aminolysis of Unactivated Esters using MnCl₂ in Combination with strong Bases as Catalyst
  作者：Nadja E. Niggli、Tobias Vollgraff、Christian Winter、Desislava Slavcheva Petkova、Stefan Benson、Roland Götz、A. Stephen K. Hashmi、Thomas Schaub

  DOI：10.1002/adsc.202300285

  日期：2023.6.13

  crop protection. Although of great interest, the atom- and step economic formation of the amide bond between a less nucleophilic aniline with an acid or ester remains still a major challenge. Herein, we report an aminolysis of aromatic and alkyl esters with anilines catalyzed by a readily available catalytic system comprising of an earth-abundant Mn-salt in combination with an inexpensive base.

  苯胺类化合物通常存在于药物和作物保护的活性成分中。尽管非常有趣，但亲核性较低的苯胺与酸或酯之间的酰胺键的原子和步骤经济形成仍然是一个主要挑战。在此，我们报告了芳香族和烷基酯与苯胺的氨解反应，该反应由一种现成的催化体系催化，该催化体系包含一种地球上丰富的锰盐和一种廉价的碱。
• <scp>Iron‐Catalyzed</scp> Amide Bond Formation from Carboxylic Acids and Isocyanates^†
  作者：Lingjian Zi、Jing Zhang

  DOI：10.1002/cjoc.202300396

  日期：2023.12

  We describe an iron-catalyzed amide bond formation from readily available carboxylic acids and isocyanates. This method utilizes an abundant and biocompatible iron catalyst and easily accessible starting materials, generates CO2 as the only byproduct, and features broad substrate scopes with good functional group compatibility. Therefore, it provides a cost-effective and practical protocol to access

  我们描述了由容易获得的羧酸和异氰酸酯形成的铁催化酰胺键。该方法利用丰富且生物相容的铁催化剂和易于获得的起始原料，产生CO 2作为唯一的副产物，并且具有广泛的底物范围和良好的官能团相容性。因此，它提供了一种经济有效且实用的方案来获取多种酰胺。
• Analysis of intermolecular interactions involving halogens in substituted benzanilides
  作者：D. Chopra、T.N. Guru Row

  DOI：10.1016/j.molstruc.2004.03.011

  日期：2005.1

  Crystal structures of halogen-substituted benzanilides have been analyzed in terms of weak interactions involving halogens. The four compounds namely 3-fluoro-N-(3-hydroxyphenyl)benzamide, 3-chloro-N-(3-hydroxyphenyl)benzamide, 3-fluoro-N-(4-methylphenyl)benzamide and 3-chloro-N-(4-methylphenyl)benzamide crystallize in monoclinic symmetry. The packing modes in the crystalline lattice generate motifs via N-(HO)-O-... and O-(HO)-O-... hydrogen bonds in structures 1 and 2 and via N-(HO)-O-... hydrogen bond, weak C-H... F and (ClCl)-Cl-... interactions in structures 3 and 4. These structures when compared with the polymorphs of benzanilide show no orientational disorder and depict subtle conformational changes, which are directed by both strong hydrogen bonds and weak interactions involving halogens. (C) 2004 Elsevier B.V. All rights reserved.
• [EN] SULFONYL ARYL HYDROXAMATES AND THEIR USE AS MATRIX METALLOPROTEASE INHIBITORS<br/>[FR] SULFONYL ARYL HYDROXAMATES ET LEUR UTILISATION COMME INHIBITEURS DES METALLOPROTEASES MATRICIELLES
  申请人：PHARMACIA CORP

  公开号：WO2003007954A2

  公开（公告）日：2003-01-30

  The invention is directed to sulfonyl aromatic hydroxamic acid compounds and salts thereof that, inter alia, inhibit matrix metalloprotease (MMP) activity and/or aggrecanase activity. In some particularly preferred embodiments, the compound corresponds in structure to one of the following formulas: (I) (II) wherein W2, the R groups, and -A-R-E-Y are described in more detail in Applicants'specification. This invention also is directed to a process that comprises administering such a compound or pharmaceutically acceptable salt thereof to a host animal having a condition associated with MMP activity.