N-(5-bromo-2-(pyridin-2-yl)phenyl)benzamide | 1581756-76-4

• 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-bromo-2-(pyridin-2-yl)phenyl)benzamide
• 英文别名: N-(5-broro-2-(pyridin-2-yl)phenyl)benzamide；N-[5-bromo-2-(pyridin-2-yl)phenyl]benzamide
• CAS: 1581756-76-4
• 化学式: C₁₈H₁₃BrN₂O
• 分子量: 353.218
• InChiKey: CISFBYCEGWADCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-溴吡啶 在 silver hexafluoroantimonate 、 四(三苯基膦)钯 、 (p-cymene)ruthenium(II) chloride 、 邻硝基苯甲酸 、 sodium carbonate 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 36.0h， 生成 N-(5-bromo-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
• [Cp*Rh ^III ]/Ionic Liquid as a Highly Efficient and Recyclable Catalytic Medium for C−H Amidation
  作者：Qiang Ma、Xinling Yu、Ruizhi Lai、Songyang Lv、Weiyang Dai、Chen Zhang、Xiaolong Wang、Qiantao Wang、Yong Wu

  DOI：10.1002/cssc.201801287

  日期：2018.10.24

  A [Cp*RhIII]‐catalyzed direct C−H amidation is carried out in ionic liquid. Both C(sp2)−H bonds of (hetero)arenes and alkenes and unactivated C(sp3)−H bonds can be easily amidated with high functional‐group tolerance and excellent yields under these conditions. Notably, using [Cp*RhIII]/[BMIM]BF4 (BMIM=1‐butyl‐3‐methylimidazolium) as the green and recyclable medium is environmentally benign, in light

  [Cp * Rh III ]催化的直接CHH酰胺化反应在离子液体中进行。在这些条件下，（杂）芳烃和烯烃的C（sp 2）-H键和未活化的C（sp 3）-H键都容易被酰胺化，具有很高的官能团耐受性和优异的收率。值得注意的是，考虑到诸如昂贵的铑催化剂的可重复使用性等特性，使用[Cp * Rh III ] / [BMIM] BF 4（BMIM = 1-丁基-3-甲基咪唑鎓）作为绿色且可回收的介质对环境无害。避免剧毒的有机溶剂，温和的反应条件以及较短的反应时间。
• <i>N</i>-Methoxyamide: An Alternative Amidation Reagent in the Rhodium(III)-Catalyzed C–H Activation
  作者：Chao Zhou、Junqi Zhao、Weicong Guo、Jijun Jiang、Jun Wang

  DOI：10.1021/acs.orglett.9b03357

  日期：2019.12.6

  In the field of transition-metal-catalyzed C-H activation, N-methoxyamides are widely used as C-H activation substrate. Unexpectedly, in this work N-methoxyamides were found to work as efficient amidation reagents in the rhodium(III)-catalyzed C-H activation with boric acid as a cocatalyst. This reaction features broad substrate scope and good yields.

  在过渡金属催化的CH活化领域中，N-甲氧基酰胺被广泛用作CH活化底物。出乎意料的是，在这项工作中，发现了N-甲氧基酰胺在以硼酸为助催化剂的铑（III）催化的CH活化中作为有效的酰胺化试剂。该反应具有广泛的底物范围和良好的收率。
• 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.