2-acetamido-N-phenylbenzamide | 54364-31-7

• 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-acetamido-N-phenylbenzamide
• 英文别名: N-Acetyl-anthranilsaeure-anilid
• CAS: 54364-31-7
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: NEHCFGBSQGPKHP-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  401.3±28.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.2
• 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-acetamido-N-phenylbenzamide 在 三甲基氯硅烷 、 sodium acetate 、 三乙胺 作用下， 以 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 11.0h， 生成 2-(p-Methoxyphenethylene)-3-phenyl-4(3H)-quinazolinone
  参考文献：
  名称：

  Synthesis of N-Heteropolycyclic Compounds Including Quinazolinone Skeleton Using Friedel–Crafts Alkylation

  摘要：

  A simple method to synthesize N-heteropolycyclic quinazolinones was developed including Knoevenagel condensation of quinazolines and aldehydes and Friedel-Craft alkylation as key steps. Knoevenagel reaction of 2-methyl-3-phenylquinazolin-4(3H)-one proceeded smoothly under a basic condition and subsequent Friedel-Craft alkylation with BrOnsted acid gave the N-heteropolycyclic quinazolinones in good yields. Furthermore, these new polycyclic compounds were converted into organic molecules having a long -conjugation system by treatment of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to utilize them as organic dyes.

  DOI：

  10.1080/00397911.2014.987353
• 作为产物：
  描述：

  2-硝基-N-苯基苯甲酰胺 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 40.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 2-acetamido-N-phenylbenzamide
  参考文献：
  名称：

  Synthesis of N-Heteropolycyclic Compounds Including Quinazolinone Skeleton Using Friedel–Crafts Alkylation

  摘要：

  A simple method to synthesize N-heteropolycyclic quinazolinones was developed including Knoevenagel condensation of quinazolines and aldehydes and Friedel-Craft alkylation as key steps. Knoevenagel reaction of 2-methyl-3-phenylquinazolin-4(3H)-one proceeded smoothly under a basic condition and subsequent Friedel-Craft alkylation with BrOnsted acid gave the N-heteropolycyclic quinazolinones in good yields. Furthermore, these new polycyclic compounds were converted into organic molecules having a long -conjugation system by treatment of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to utilize them as organic dyes.

  DOI：

  10.1080/00397911.2014.987353

文献信息

• Expedient Synthesis of <i>N</i>-Acyl Anthranilamides and β-Enamine Amides by the Rh(III)-Catalyzed Amidation of Aryl and Vinyl C–H Bonds with Isocyanates
  作者：Kevin D. Hesp、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ja203495c

  日期：2011.8.3

  A Rh(III)-catalyzed protocol for the amidation of anilide and enamide C-H bonds with isocyanates has been developed. This method provides direct and efficient syntheses of N-acyl anthranilamides, enamine amides, and pyrimidin-4-one heterocycles.

  已经开发了一种用于将苯胺和烯酰胺 CH 键与异氰酸酯酰胺化的 Rh(III) 催化方案。该方法直接有效地合成了 N-酰基邻氨基苯甲酰胺、烯胺酰胺和嘧啶-4-一杂环。
• Towards a Sequential One-Pot Preparation of 1,2,3-Benzotriazin-4(3<i>H</i> )-ones Employing a Key Cp*Co(III)-catalyzed C−H Amidation Step
  作者：Paula G. Chirila、Lauren Skibinski、Keith Miller、Alex Hamilton、Christopher J. Whiteoak

  DOI：10.1002/adsc.201800133

  日期：2018.6.15

  initial C−H amidation step, leading to the overall development of a facile one‐pot procedure for the preparation of a range of substituted 1,2,3‐benzotriazin‐4(3H)‐one derivatives, requiring only 5 hours of reaction time, which is also applicable on a gram scale. In addition, the key Cp*Co(III)‐catalyzed C−H amidation step has been studied by DFT calculations in order to fully elucidate the mechanism.

  1,2,3-苯并三嗪-4（3 H）-一衍生物因其潜在用途而被公认为是农药和药物，因此从易于获得的试剂开始的新制备方法将是一个诱人的主张。各种不同取代的苯甲酰胺很容易获得，它们为直接的CH功能化方案的应用提供了出色的底物支架。在这种情况下，我们在此报告了使用Cp * Co（III）催化剂酰胺化这些苯甲酰胺，使用1,4,2-二恶唑-5-酮作为酰胺化剂。该可分离的中间体2-乙酰氨基苯甲酰胺的产品可随后转化成所需的1,2,3-苯并三嗪-4（3 H ^）通过使用-酮衍生物叔亚硝酸丁酯在温和的条件下。发现可以使用从初始CH酰胺化步骤获得的粗制反应混合物进行第二步，从而全面开发了一种简便的单锅法，用于制备一系列取代的1,2， 3-苯并三嗪-4（3 H）-一衍生物，仅需5个小时的反应时间，也适用于克级。此外，通过DFT计算研究了关键的Cp * Co（III）催化的CH酰胺化步骤，以充分阐明其机理。
• Synthesis of 4<i>H</i>-3,1-benzoxazin-4-ones and 4-(3<i>H</i>)quinazolinones from anthranilic acids and their derivatives by the use of triphenyl phosphite and pyridine
  作者：Guy Rabilloud、Bernard Sillion

  DOI：10.1002/jhet.5570170542

  日期：1980.7

  A series of 2-substituted 4H-3,1-benzoxazinones and 2,3-disubstituted 4-(3H)quinazolinones have been synthesized in mild conditions by the use of triphenyl phosphite and pyridine as cyclising medium. Benzox-azinones are produced either by ring closure of 2-(acylamino)benzoic acids or in the reaction of benzoic acid with anthranilic acids. In the presence of aniline, the reaction leads to quinazolinones

  通过使用亚磷酸三苯酯和吡啶作为环化介质，在温和条件下合成了一系列2取代的4 H -3,1-苯并恶嗪酮和2,3-二取代的4-（3 H）喹唑啉酮。通过2-（酰基氨基）苯甲酸的闭环或在苯甲酸与邻氨基苯甲酸的反应中生产苯并-叠氮酮。在苯胺存在下，该反应产生喹唑啉酮。
• Ruthenium‐Catalyzed Aminocarbonylation with Isocyanates Through Weak Coordinating Groups
  作者：Elisa Y. Lai、Binbin Yuan、Lutz Ackermann、Magnus J. Johansson

  DOI：10.1002/chem.202302023

  日期：2023.11.2

  Introducing amide functional groups under mild conditions has growing importance owing to the prevalence of such moiety in biologically active molecules. Herein, we disclose a mild protocol for the directed ruthenium‐catalyzed C−H aminocarbonylation with isocyanates as the amidating agents developed through high‐throughput experimentation (HTE). The redox‐neutral and base‐free reaction is guided by weakly Lewis basic functional groups, including anilides, lactams and carbamates to access anthranilamide derivatives. The synthetic utility of this transformation is reflected by large‐scale synthesis and late‐stage functionalization.

  摘要由于生物活性分子中普遍存在酰胺官能团，因此在温和条件下引入酰胺官能团的重要性与日俱增。在此，我们通过高通量实验（HTE）公开了一种温和的以异氰酸酯为酰胺化剂的定向钌催化 C-H 氨基羰基化反应方案。在弱路易斯碱性官能团（包括苯胺类、内酰胺类和氨基甲酸酯类）的引导下，这种氧化还原中性的无碱反应可获得蒽酰胺衍生物。大规模合成和后期功能化体现了这种转化的合成效用。
• Synthesis of 3-Substituted and 2,3-Disubstituted Quinazolinones via Cu-Catalyzed Aryl Amidation
  作者：Lanting Xu、Yongwen Jiang、Dawei Ma

  DOI：10.1021/ol300084v

  日期：2012.2.17

  Cul/4-hydroxy-L-proline catalyzed coupling of N-substituted o-bromobenzamides with formamide takes place at 80 degrees C, affording 3-substituted quinazolinones directly. Under these conditions other amides that were tested only provided simple coupling products, which can be converted into 2,3-disubstituted quinazolinones via HMDS/ZnCl2 mediated condensative cyclization.