2-iodo-N-(2-bromophenyl)benzamide | 313268-50-7

• 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-iodo-N-(2-bromophenyl)benzamide
• 英文别名: N-(2-bromophenyl)-2-iodobenzamide；2-iodo-N-(2-bromoaryl)-benzamide
• CAS: 313268-50-7
• 化学式: C₁₃H₉BrINO
• mdl: MFCD01839703
• 分子量: 402.029
• InChiKey: GZTNPAOTLWMQRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-iodo-N-(2-bromophenyl)benzamide 在 selenium 、 copper(l) iodide 、 1,10-菲罗啉 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以93%的产率得到2-(2-bromophenyl)-1,2-benzisoselenazol-3(2H)-one
  参考文献：
  名称：

  Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones

  摘要：

  Scope of the copper catalyzed/mediated selenium-nitrogen coupling reaction has been studied for the synthesis of isoselenazolones. It is noticed that the 2-chloro, 2-bromo-, and 2-iodo-aryl amides substrates can be exploited in the selenium-nitrogen coupling reaction by employing 25-100 mol % of CuI/1,10-phenanthroline (L) and potassium carbonate as a base in DMF. Furthermore, electron rich 2-chloro-arylamides also underwent selenium-nitrogen coupling reaction to give biologically important selenium-nitrogen heterocycles. Also, copper-catalyzed selenium-nitrogen coupling reaction has been meticulously applied for the synthesis of diaryl diselenides having methoxy, amine, and amide functionality from respective aryl iodides in the presence of stoichiometric amount of succinimide as an external Se-N coupling partner. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.141
• 作为产物：
  描述：

  邻碘苯甲酰氯 、 2-溴苯胺 以 二氯甲烷 为溶剂， 以93%的产率得到2-iodo-N-(2-bromophenyl)benzamide
  参考文献：
  名称：

  Cu-Catalyzed Efficient Synthetic Methodology for Ebselen and Related Se−N Heterocycles

  摘要：

  An efficient copper-catalyzed method for the synthesis of biologically important ebselen and related analogues containing a Se-N bond has been developed. This is the first report of a catalytic process of selenation and Se-N bond formation reaction. Copper-catalyzed reaction tolerates functional groups such as amides, hydroxyls, ethers, nitro, fluorides, and chlorides. The best results are obtained by using a combination of potassium carbonate as a base, Iodo- or bromo-arylamide substrates, selenium powder, and copper iodide catalyst.

  DOI：

  10.1021/ol102027j

文献信息

• Pd/C-Catalyzed Homocoupling Reaction for the Synthesis of Symmetrical Biaryl Diamides
  作者：Guodong Shen、Bingchuan Yang、Yichen Wang、Xiliang Zhao、Xinlei Huangfu、Yanmeng Tian、Tongxin Zhang

  DOI：10.1055/s-0036-1588437

  日期：2017.9

  Pd/C was found to be an efficient and convenient metal catalyst in the homocoupling reaction for the synthesis of symmetrical biaryl diamides. The catalyst system Pd/C–KOAc showed high catalytic activity, and a variety of symmetrical biaryl diamides were conveniently synthesized from 2-halo- N -phenylbenzamides in moderate to good yields.

  发现 Pd/C 在合成对称联芳基二酰胺的均偶联反应中是一种有效且方便的金属催化剂。催化剂体系 Pd/C-KOAc 显示出高催化活性，并且可以从 2-卤代-N-苯基苯甲酰胺以中等至良好的产率方便地合成各种对称的联芳基二酰胺。
• Synthesis, structures and electrochemical and photophysical properties of anilido-benzoxazole boron difluoride (ABB) complexes
  作者：Yedukondalu Meesala、Veerababurao Kavala、Hao-Ching Chang、Ting-Shen Kuo、Ching-Fa Yao、Way-Zen Lee

  DOI：10.1039/c4dt03052d

  日期：——

  CH2Cl2) and in the solid-state (Φf = 0.07–0.37). These complexes show a larger Stokes shift (56–128 nm) than the well-known boron dipyrromethene dyes (8–12 nm, in most cases). The role of molecular packing patterns elucidated by the assistance of their X-ray crystal structures rationalizes the solid-state fluorescence. One of the tested compounds displayed aggregation induced emission (AIE). First-principle-based

  通过在温和的反应条件下使用不对称的双齿配体合成了一系列新的四环稠合的π-共轭π-苯胺-苯并恶唑二氟化硼（ABB）染料。X射线结构分析表明，四环稠合的π-共轭骨架几乎共面，并且几乎与侧苯胺基苯基正交，二面角为74-86°。将合成复合物在溶液中表现出非常明亮的发光（Φ ˚F = 0.45-0.96的CH 2氯2）和在固体状态（Φ ˚F= 0.07–0.37）。这些复合物比著名的硼二吡咯亚甲基染料（大多数情况下为8–12 nm）显示出更大的斯托克斯位移（56–128 nm）。借助其X射线晶体结构阐明的分子堆积图样的作用使固态荧光合理化。被测化合物之一显示出聚集诱导发射（AIE）。基于第一原理的量子化学研究是在配合物1-6上进行的。与时间有关的DFT（TD-DFT）计算支持实验结果。发现苯胺苯基部分和氟原子的参与在LUMO轨道中可忽略不计。
• 10.1002/anie.202407979
  作者：Sephton, Thomas、Large, Jonathan M.、Natrajan, Louise S.、Butterworth, Sam、Greaney, Michael F.

  DOI：10.1002/anie.202407979

  日期：——

  A photocatalytic, XAT mediated Smiles-Truce biaryl synthesis is described. The reaction uses mild methods to generate and chemoselectively harness capricious aryl radicals, efficiently furnishing valuable biaryl products. The reaction utilises a simple yet underexplored amide linker, which enables a challenging formal C−N arylation of anilines.

  描述了光催化、XAT 介导的 Smiles-Truce 联芳基合成。该反应采用温和的方法来生成和化学选择性地利用反复无常的芳基自由基，有效地提供有价值的联芳基产物。该反应利用了一个简单但尚未充分研究的酰胺连接体，可实现苯胺的具有挑战性的形式 C−N 芳基化。
• Supported-Pd catalyzed carbonylative synthesis of phthalimides and isoindolinones using Oxalic acid as in situ CO surrogate with 2-iodobenzamides and 2-iodobenzylanilines in ppm-level catalyst loading
  作者：Shankar Ram、Pushkar Mehara、Ashish Kumar、Ajay Kumar Sharma、Arvind Singh Chauhan、Ajay Kumar、Pralay Das

  DOI：10.1016/j.mcat.2022.112606

  日期：2022.9
• Cu-Catalyzed Efficient Synthetic Methodology for Ebselen and Related Se−N Heterocycles
  作者：Shah Jaimin Balkrishna、Bhagat Singh Bhakuni、Deepak Chopra、Sangit Kumar

  DOI：10.1021/ol102027j

  日期：2010.12.3

  An efficient copper-catalyzed method for the synthesis of biologically important ebselen and related analogues containing a Se-N bond has been developed. This is the first report of a catalytic process of selenation and Se-N bond formation reaction. Copper-catalyzed reaction tolerates functional groups such as amides, hydroxyls, ethers, nitro, fluorides, and chlorides. The best results are obtained by using a combination of potassium carbonate as a base, Iodo- or bromo-arylamide substrates, selenium powder, and copper iodide catalyst.