N'-(4-bromophenyl)ethanimidamide

• 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'-(4-bromophenyl)ethanimidamide
• 化学式: C₈H₉BrN₂
• 分子量: 213.077
• InChiKey: PUCLIECJJRKSEZ-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'-(4-bromophenyl)ethanimidamide 、 2-溴丙二醛 在 溶剂黄146 、 三乙胺 作用下， 以 异丙醇 为溶剂， 反应 1.0h， 以91%的产率得到1-(4-溴苯基)-2-甲基-1H-咪唑-5-甲醛
  参考文献：
  名称：

  Synthesis and evaluation of new difluoromethyl azoles as antileishmanial agents

  摘要：

  Several compounds of great pharmacological interest contain the triazole and imidazole rings. In order to find new drugs with antileishmanial activity we have synthesized and evaluated new imidazole and triazole compounds carrying either the carbaldehyde or the difluoromethylene functionalities against promastigote forms of Leishmania amazonensis. Among the compounds tested difluoromethylene azoles 4b and 8f have inhibited the parasite growth significantly. Our results show that the introduction of the difluoromethylene moieties has turned the inactive carbaldehydes into active antileishmanial compounds. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.020
• 作为产物：
  描述：

  乙腈 、 4-溴苯胺 在 aluminum (III) chloride 作用下， 反应 3.0h， 生成 N'-(4-bromophenyl)ethanimidamide
  参考文献：
  名称：

  通过Rh（III）催化的酰胺基和蒽基的CH活化级联反应实际合成苯并咪唑并[1,2-a]喹啉。

  摘要：

  我们报告新颖和实用的一锅Rh（III）催化的战略，从容易获得的亚酰胺和邻氨基苯甲酸构造苯并咪唑并[1,2-a]喹啉。该级联反应是通过在不添加任何添加剂的离子液体中通过CH胺化-环化-环化过程进行的，并且操作简单，产率中等至高，并且具有广泛的底物范围特征，将为构建具有生物活性的稠合苯并咪唑提供参考。

  DOI：

  10.1021/acs.orglett.9b04256

文献信息

• Rh(III)-Catalyzed Synthesis of <i>N</i>-Unprotected Indoles from Imidamides and Diazo Ketoesters via C–H Activation and C–C/C–N Bond Cleavage
  作者：Zisong Qi、Songjie Yu、Xingwei Li

  DOI：10.1021/acs.orglett.5b03669

  日期：2016.2.19

  The synthesis of N-unprotected indoles has been realized via Rh(III)-catalyzed C–H activation/annulation of imidamides with α-diazo β-ketoesters. The reaction occurs with the release of an amide coproduct, which originates from both the imidamide and the diazo as a result of C═N cleavage of the imidamide and C–C(acyl) cleavage of the diazo. A rhodacyclic intermediate has been isolated and a plausible

  N-未保护的吲哚的合成已通过Rh（III）催化的C-H活化/亚酰胺与α-重氮β-酮酸酯的环化而实现。反应发生时会发生酰胺副产物的释放，酰胺副产物既来自亚酰胺也来自重氮，这是由于亚胺的C═N裂解和重氮的C–C（酰基）裂解所致。分离了一个rhodocyclic中间体，并提出了一个合理的机制。
• Ruthenium(II)‐Catalyzed C−H Activation of Imidamides and Divergent Couplings with Diazo Compounds: Substrate‐Controlled Synthesis of Indoles and 3 <i>H</i> ‐Indoles
  作者：Yunyun Li、Zisong Qi、He Wang、Xifa Yang、Xingwei Li

  DOI：10.1002/anie.201606316

  日期：2016.9.19

  Indoles are an important structural motif that is commonly found in biologically active molecules. In this work, conditions for divergent couplings between imidamides and acceptor–acceptor diazo compounds were developed that afforded NH indoles and 3H‐indoles under ruthenium catalysis. The coupling of α‐diazoketoesters afforded NH indoles by cleavage of the C(N2)−C(acyl) bond whereas α‐diazomalonates

  吲哚是生物活性分子中常见的重要结构基序。在这项工作中，开发了酰亚胺酰胺和受体-受体重氮化合物之间发散偶联的条件，该条件可在钌催化下提供NH吲哚和3 H-吲哚。α-二氮杂酮酸酯的偶联通过裂解C（N 2）-C（酰基）键提供了NH吲哚，而α-二氮杂丙二酸酯通过C-N键的裂解产生了3个H-吲哚。该反应通过钌催化的CH活化作用构成重氮底物与芳烃的第一个分子间偶联。
• Synthesis of indoles and quinazolines <i>via</i> additive-controlled selective C–H activation/annulation of <i>N</i>-arylamidines and sulfoxonium ylides
  作者：Ruizhi Lai、Xiaohua Wu、Songyang Lv、Chen Zhang、Maoyao He、Yuncan Chen、Qiantao Wang、Li Hai、Yong Wu

  DOI：10.1039/c9cc01146c

  日期：——

  Selective synthesis of indoles and quinazolines was achieved through a precise control of C–H activation/annulation by changing additives.

  通过改变添加剂，通过精确控制C-H活化/环化实现了对吲哚和喹唑啉的选择性合成。
• Synthesis of 2-Substituted Quinolines <i>via</i> Rhodium(III)-Catalyzed C-H Activation of Imidamides and Coupling with Cyclopropanols
  作者：Xukai Zhou、Zisong Qi、Songjie Yu、Lingheng Kong、Yang Li、Wan-Fa Tian、Xingwei Li

  DOI：10.1002/adsc.201601278

  日期：2017.5.17

  An efficient synthesis of 2-substituted quinolines from readily available cyclopropanols and imidamides has been developed, where the cyclopropanol acts as a C3 synthon. With the assistance of a bifunctional imidamide directing group, the reaction occurred via sequential C–H/C–C cleavage and C–C/C–N bond formation.

  已经开发了从容易获得的环丙醇和酰亚胺酰胺有效合成2-取代的喹啉的方法，其中环丙醇充当C 3合成子。在双官能的酰亚胺酰胺导向基团的协助下，反应通过顺序的C–H / C–C裂解和C–C / C–N键形成而发生。
• 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。