N'-(2-bromophenyl)acetimidamide | 1262137-06-3

• 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'-(2-bromophenyl)acetimidamide
• 英文别名: N'-(2-bromophenyl)ethanimidamide
• CAS: 1262137-06-3
• 化学式: C₈H₉BrN₂
• 分子量: 213.077
• InChiKey: WMEJBICXBCPSTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N'-(2-bromophenyl)acetimidamide 在 copper(I) oxide 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 水 为溶剂， 反应 30.0h， 以78%的产率得到2-甲基苯并咪唑
  参考文献：
  名称：

  Copper-Catalyzed Intramolecular C−N Bond Formation: A Straightforward Synthesis of Benzimidazole Derivatives in Water

  摘要：

  A straightforward, efficient, and more sustainable copper-catalyzed method has been developed for intramolecular N-arylation providing the benzimidazole ring system. With Cu2O (5 mol %) as the catalyst, DMEDA (10 mol %) as the ligand, and K2CO3 as the base, this protocol was applied to synthesize a small library of benzimidazoles in high yields. Remarkably, the reaction was exclusively carried out in water, rendering the methodology highly valuable from both environmental and economical points of view.

  DOI：

  10.1021/jo1021426
• 作为产物：
  描述：

  乙腈 、 2-溴苯胺 在 aluminum (III) chloride 作用下， 生成 N'-(2-bromophenyl)acetimidamide
  参考文献：
  名称：

  铑 (III) 催化的 N-芳基脒与碘叶立德的发散 C−H 官能化：获得咔唑啉酮和两性离子盐

  摘要：

  我们描述了铑 (III) 催化的N-芳基脒与碘叶立德的发散 C-H 键功能化。在不同的反应条件下，通过分子间环化和分子内质子转移，可以不同地构建咔唑啉酮和两性离子盐。该协议操作简单，可以容忍各种功能组。药物分子的高效后修饰证明了其实用性。

  DOI：

  10.1002/adsc.202201390

文献信息

• Synthesis of 4-Aminoquinazolines by Palladium-Catalyzed Intramolecular Imidoylation of N-(2-Bromoaryl)amidines
  作者：Gitte Van Baelen、Sander Kuijer、Lukáš Rýček、Sergey Sergeyev、Elwin Janssen、Frans J. J. de Kanter、Bert U. W. Maes、Eelco Ruijter、Romano V. A. Orru

  DOI：10.1002/chem.201102468

  日期：2011.12.23

  investigated the intramolecular imidoylative cross‐coupling of N‐(2‐bromoaryl)amidines, leading to 4‐aminoquinazolines. After thorough optimization of the reaction with respect to palladium source and loading, ligand, base, temperature, and solvent, a small library of 4‐aminoquinazolines was prepared to determine the scope of this method. Various substituents are tolerated on the amidine and the isocyanide

  与广泛使用羰基化Pd催化的交叉偶联反应相比，涉及异氰酸酯插入的类似反应几乎处于空白。我们研究了N-（2-溴芳基）am的分子内酰亚胺化交叉偶联，从而导致了4-氨基喹唑啉。在对钯源和负载，配体，碱，温度和溶剂的反应进行了全面优化之后，准备了一个小的4-氨基喹唑啉文库来确定该方法的范围。idine和异氰酸酯上可以容忍各种取代基，从而有效地获得了广泛的具有广泛药学意义的各种取代的4-氨基喹唑啉。
• Copper-Catalyzed Intramolecular C−N Bond Formation: A Straightforward Synthesis of Benzimidazole Derivatives in Water
  作者：Jinsong Peng、Min Ye、Cuijuan Zong、Fangyun Hu、Lingtong Feng、Xiaoyan Wang、Yufeng Wang、Chunxia Chen

  DOI：10.1021/jo1021426

  日期：2011.1.21

  A straightforward, efficient, and more sustainable copper-catalyzed method has been developed for intramolecular N-arylation providing the benzimidazole ring system. With Cu2O (5 mol %) as the catalyst, DMEDA (10 mol %) as the ligand, and K2CO3 as the base, this protocol was applied to synthesize a small library of benzimidazoles in high yields. Remarkably, the reaction was exclusively carried out in water, rendering the methodology highly valuable from both environmental and economical points of view.
• Rhodium(III)‐Catalyzed Divergent C−H Functionalization of <i>N</i> ‐Aryl Amidines with Iodonium Ylides: Access to Carbazolones and Zwitterionic Salts
  作者：Jie Ren、Liu Yang、Chao Pi、Xiuling Cui、Yangjie Wu

  DOI：10.1002/adsc.202201390

  日期：——

  We described an Rhodium(III)-catalyzed divergent C−H bond functionalization of N-aryl amidines with iodonium ylides. Carbazolones and zwitterionic salts were diversely constructed through intermolecular annulation and intramolecular proton transfer under the different reaction conditions. This protocol is operationally simple and tolerates a variety of functional groups. The efficient post-modification

  我们描述了铑 (III) 催化的N-芳基脒与碘叶立德的发散 C-H 键功能化。在不同的反应条件下，通过分子间环化和分子内质子转移，可以不同地构建咔唑啉酮和两性离子盐。该协议操作简单，可以容忍各种功能组。药物分子的高效后修饰证明了其实用性。