N-(3-氯-4-氟苯基)苯甲酰胺 | 64141-28-2

• 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: N-(3-氯-4-氟苯基)苯甲酰胺
• 英文名称: N-(3-chloro-4-fluorophenyl)benzamide
• CAS: 64141-28-2
• 化学式: C₁₃H₉ClFNO
• mdl: MFCD01182211
• 分子量: 249.672
• InChiKey: KDWBMZLQPODRSV-UHFFFAOYSA-N

物化性质

• 沸点：
  276.0±30.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 氧气 作用下， 以 丙酮 为溶剂， 反应 35.0h， 以68%的产率得到N-(3-氯-4-氟苯基)苯甲酰胺
  参考文献：
  名称：

  使用可见光诱导的光氧化还原催化的 N,N-二苄基苯胺的非水氧化 C–N 裂解区域选择性合成 2°酰胺

  摘要：

  据报道，可见光驱动的光氧化还原催化的N , N -二苄基苯胺的非水氧化 C-N 裂解为 2° 酰胺。此外，我们已将此协议应用于 2-(二苄基氨基) 苯甲酰胺以提供具有 (NH 4 ) 2 S 2 O 8作为添加剂的喹唑啉酮。机理研究表明，该反应可能通过 C-N 键断裂，然后加入超氧离子形成酰胺，原位生成 α-氨基自由基为亚胺。

  DOI：

  10.1021/acs.joc.1c01792

文献信息

• Direct amide synthesis <i>via</i> Ni-mediated aminocarbonylation of arylboronic acids with CO and nitroarenes
  作者：Ni Shen、Chi Wai Cheung、Jun-An Ma

  DOI：10.1039/c9cc06638a

  日期：——

  Herein we describe an alternative and unconventional approach of an aminocarbonylation reaction to access aryl amides from readily available and low-cost arylboronic acids and nitroarenes. Nickel metal can serve as both reductant and catalyst in this direct aminocarbonylation. This protocol exhibits a good functional group compatibility and allows a variety of aryl amides to be synthesized, including

  本文中，我们描述了一种氨基羰基化反应的替代性和非常规方法，可从容易获得的低成本芳基硼酸和硝基芳烃中获得芳基酰胺。在这种直接的氨基羰基化反应中，镍金属既可以充当还原剂，又可以充当催化剂。该方案显示出良好的官能团相容性，并允许合成多种芳基酰胺，包括几种药物样分子。
• Room-Temperature Debenzylation of <i>N</i>-Benzylcarboxamides by<i> N</i>-Bromosuccinimide
  作者：Ke Ding、Liping Kuang、Jing Zhou、Sheng Chen

  DOI：10.1055/s-2007-990795

  日期：2007.10

  A simple and highly efficient method has been developed with which to cleave the N-benzyl group on N-mono- or di­substituted carboxamides using N-bromosuccinimide (NBS) at room temperature. All the 31 substrates examined showed moderate to excellent deprotection yields. Our study also indicated that the debenzylation may involve an oxygen/light initiated free radical mechanism.

  开发了一种简单且高效的方法，可以在室温下使用N-溴琥珀酰亚胺（NBS）去除N-单取代或双取代羧酰胺上的N-苄基基团。所有31种被检验的底物表现出中等到优秀的去保护产率。我们的研究还表明，去苄基化可能涉及氧/光引发的自由基机制。
• <i>N,N</i>′-Carbonyldiimidazole-Mediated Amide Coupling: Significant Rate Enhancement Achieved by Acid Catalysis with Imidazole·HCl
  作者：Emily K. Woodman、Julian G. K. Chaffey、Philip A. Hopes、David R. J. Hose、John P. Gilday

  DOI：10.1021/op800226b

  日期：2009.1.16

  Over a series of 10 aromatic amines we show the rate of CDT mediated amidation to be significantly enhanced upon introduction of imidazole center dot HCl as a proton source for acid catalysis. Our work supports and provides an application for previous investigations into the imidazolium effect, thus increasing the scope of CDT as an amide-coupling reagent with aromatic amines. The influence of the relative pK(a) of the amines studied on the rate of reaction was also investigated.
• Molecular modeling studies, synthesis and biological evaluation of derivatives of N-phenylbenzamide as Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitors
  作者：Kumar R. Desai、Mushtaque S. Shaikh、Evans C. Coutinho

  DOI：10.1007/s00044-010-9323-4

  日期：2011.4

  The search for new antimalarial agents is necessary as current drugs in the market have become vulnerable due to the emergence of resistant strains of Plasmodium falciparum (Pf). The enzyme dihydroorotate dehydrogenase (PfDHODH) is a validated target for development of antimalarial agents. PfDHODH is a crucial enzyme in the de novo pyrimidine biosynthesis pathway and is essential for the growth of the parasite. In this article, we report the design, synthesis and evaluation of benzanilides as inhibitors of PfDHODH. From the pool of molecules designed using molecular modeling techniques, candidates were shortlisted for further evaluation based on docking scores and 3D-QSAR studies. The activities of these shortlisted analogs were predicted from CoMFA and CoMSIA models. The most promising molecules were synthesized using solvent-free microwave-assisted synthesis and their structures characterized by spectroscopic techniques. The molecules were screened for in vitro antimalarial activity by the whole cell assay method. Two molecules viz. KMC-3 and KMC-15 were found to be active at 8.7 and 5.7 mu M concentrations, respectively.
• Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C–N Cleavage of <i>N</i>,<i>N</i>-Dibenzylanilines
  作者：Nalladhambi Neerathilingam、Mandapati Bhargava Reddy、Ramasamy Anandhan

  DOI：10.1021/acs.joc.1c01792

  日期：2021.11.5

  protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C–N bond cleavage followed by the addition of superoxide ion to form amides.

  据报道，可见光驱动的光氧化还原催化的N , N -二苄基苯胺的非水氧化 C-N 裂解为 2° 酰胺。此外，我们已将此协议应用于 2-(二苄基氨基) 苯甲酰胺以提供具有 (NH 4 ) 2 S 2 O 8作为添加剂的喹唑啉酮。机理研究表明，该反应可能通过 C-N 键断裂，然后加入超氧离子形成酰胺，原位生成 α-氨基自由基为亚胺。