N-benzyl-4-chloro-N'-phenylbenzimidamide | 1609460-27-6

• 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-benzyl-4-chloro-N'-phenylbenzimidamide
• 英文别名: N-benzyl-4-chloro-N′-phenylbenzimidamide
• CAS: 1609460-27-6
• 化学式: C₂₀H₁₇ClN₂
• 分子量: 320.821
• InChiKey: YJUVTQWTVLSEFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  24.39
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-4-chloro-N'-phenylbenzimidamide 在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以88%的产率得到1-benzyl-2-(4-chlorophenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Solvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines

  摘要：

  A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp(3))-C(sp(2)) and C(sp(2))-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp(3)C-H/sp(2)C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.

  DOI：

  10.1021/ol500864r
• 作为产物：
  描述：

  N-苄基-4-氯苯甲酰胺 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.17h， 生成 N-benzyl-4-chloro-N'-phenylbenzimidamide
  参考文献：
  名称：

  Solvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines

  摘要：

  A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp(3))-C(sp(2)) and C(sp(2))-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp(3)C-H/sp(2)C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.

  DOI：

  10.1021/ol500864r

文献信息

• Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines
  作者：Wing Cheung、Raymond J. Patch、Mark R. Player

  DOI：10.1016/j.tetlet.2018.05.019

  日期：2018.6

  4-diarylquinazolines is described which involves a silver oxide-mediated CH activation/CN bond formation process. The generality of this method with respect to substituent effects is presented along with studies leading to process optimization. Mechanistic investigations provide support for the involvement of radical intermediates in the reaction process.

  描述了合成2，4-二芳基喹唑啉的单釜法，该法涉及氧化银介导的C H活化/ C N键形成过程。提出了有关取代基效应的通用方法以及导致工艺优化的研究。机理研究为自由基中间体参与反应过程提供了支持。
• Transition Metal-Free Visible Light-Driven Photoredox Oxidative Annulation of Arylamidines
  作者：Zi-chao Shen、Pan Yang、Yu Tang

  DOI：10.1021/acs.joc.5b02366

  日期：2016.1.4

  A fast catalytic synthesis of multisubstituted quinazolines from readily available amidines via visible light-mediated oxidative C(sp(3))-C(sp(2)) bond formation has been established. This reaction is a metal-free oxidative coupling catalyzed by a photoredox organocatalyst. The protocol features low catalyst loading (1 mol %).