N-(5-formyl-2-(pyridin-2-yl)phenyl)benzamide | 1581756-80-0

• 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: N-(5-formyl-2-(pyridin-2-yl)phenyl)benzamide
• 英文别名: N-[5-formyl-2-(pyridin-2-yl)phenyl]benzamide；N-(5-formyl-2-pyridin-2-ylphenyl)benzamide
• CAS: 1581756-80-0
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: RUKAALDHABHGHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲酰氯 在 silver hexafluoroantimonate 、 sodium azide 、 (p-cymene)ruthenium(II) chloride 、 邻硝基苯甲酸 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 18.0h， 生成 N-(5-formyl-2-(pyridin-2-yl)phenyl)benzamide
  参考文献：
  名称：

  Orthogonal Reactivity of Acyl Azides in C–H Activation: Dichotomy between C–C and C–N Amidations Based on Catalyst Systems

  摘要：

  The dual reactivity of acyl azides was utilized successfully in C-H activation by the choice of catalyst systems: while selective C-C amidation was achieved under thermal Rh catalysis, a Ru catalyst was found to mediate direct C-N amidation also highly selectively. Investigations of the mechanistic dichotomy between two catalytic systems are also presented.

  DOI：

  10.1021/ol500602b

文献信息

• Mechanistic Studies on the Rh(III)-Mediated Amido Transfer Process Leading to Robust C–H Amination with a New Type of Amidating Reagent
  作者：Yoonsu Park、Kyung Tae Park、Jeung Gon Kim、Sukbok Chang

  DOI：10.1021/jacs.5b01324

  日期：2015.4.8

  bearing an amidating reagent was achieved, its facile conversion to an amido-inserted rhodacycle allowed for a clear picture on the C-H amidation process. The newly developed amidating reagent of 1,4,2-dioxazol-5-ones was applicable to a broad range of substrates with high functional group tolerance, releasing carbon dioxide as a single byproduct. Additional attractive features of this amino source, such

  对 Cp*Rh(III) 催化的直接 CH 胺化反应的机理研究使我们揭示了 1,4,2-dioxazol-5-one 及其衍生物作为高效氨基来源的新用途。CN 键形成过程的逐步分析表明，铑金属中心与酰胺化试剂或底物的竞争性结合与反应效率密切相关。在该系列中，观察到 1,4,2-二恶唑-5-酮对阳离子 Rh(III) 具有很强的亲和力，与叠氮化物相比，酰胺化效率显着提高。动力学和计算研究表明，1,4,2-dioxazol-5-one 的高酰胺化反应性除了高配位能力外，还可归因于亚氨基插入过程的低活化能。虽然实现了带有酰胺化试剂的阳离子 Cp*Rh(III) 复合物的表征，但它可以轻松转化为插入酰胺基的红丹环，从而可以清楚地了解 CH 酰胺化过程。新开发的 1,4,2-二恶唑-5-酮酰胺化试剂适用于具有高官能团耐受性的广泛底物，释放二氧化碳作为单一副产物。这种氨基源的其他吸引人的特点，例如与相
• Comparative Catalytic Activity of Group 9 [Cp*M^III] Complexes: Cobalt-Catalyzed CH Amidation of Arenes with Dioxazolones as Amidating Reagents
  作者：Juhyeon Park、Sukbok Chang

  DOI：10.1002/anie.201505820

  日期：2015.11.16

  A procedure for the [Cp*CoIII]‐catalyzed direct CH amidation of arenes with dioxazolone has been developed. This reaction proceeds under straightforward and mild conditions with a broad range of substrates, including anilides. A comparative study on the catalytic activity of Group 9 [Cp*MCl2}2] complexes revealed the unique efficiency of the cobalt catalyst.

  已经开发了用[Cp * Co III ]催化的芳烃与二恶唑酮直接CH酰胺化的方法。该反应在简单，温和的条件下与各种底物（包括酸酐）一起进行。对第9组[Cp * MCl 2 } 2 ]配合物的催化活性的比较研究表明，钴催化剂具有独特的效率。
• Cationic Cobalt(III)‐Catalyzed Aryl and Alkenyl CH Amidation: A Mild Protocol for the Modification of Purine Derivatives
  作者：Yujie Liang、Yu‐Feng Liang、Conghui Tang、Yizhi Yuan、Ning Jiao

  DOI：10.1002/chem.201503533

  日期：2015.11.9

  A cationic cobalt(III)‐catalyzed direct CH amidation of unactivated (hetero)arenes and alkenes by using 1,4,2‐dioxazol‐5‐ones as the amidating reagent has been developed. This transformation proceeds efficiently under external oxidant‐free conditions with a broad substrate scope. Moreover, 6‐arylpurine compounds, which often exhibit high potency in antimycobacterial, cytostatic, and anti‐HCV activities

  阳离子钴（III）催化的直接Ç 者H已被开发未活化的（杂）芳烃和烯烃通过使用-1,4,2-二恶唑-5-酮作为酰胺化试剂的酰胺化。这种转化在广泛的底物范围内，在无外部氧化剂的条件下有效进行。此外，通常在抗分枝杆菌，细胞生长抑制和抗HCV活性方面表现出高功效的6-芳基嘌呤化合物可以被平滑地酰胺化，从而为它们的后期功能化提供了温和的方案。
• OrthoC H amidations enabled by a recyclable manganese-ionic liquid catalytic system
  作者：Xianqiang Kong、Bo Xu

  DOI：10.1016/j.tetlet.2019.151521

  日期：2020.2

  We described an environmentally benign, recyclable base metal catalyst system (MnBr(CO)(5)/[Hmim] OAc) for ortho-C-H amidation. The readily available dioxazolones was used as the amidation agents. A broad substrate scope and high functional group tolerance were observed. The catalyst system (MnBr(CO)(5)/[Hmim]OAc) could be easily reused by simple phase separations: (C) 2019 Elsevier Ltd. All rights reserved.