N-(4-methoxybenzyl)-N′-phenylbenzimidamide | 1609460-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-methoxybenzyl)-N′-phenylbenzimidamide
• CAS: 1609460-41-4
• 化学式: C₂₁H₂₀N₂O
• 分子量: 316.403
• InChiKey: MYWSZEMTCVQBEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33.62
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzyl)-N′-phenylbenzimidamide 在 碘苯二乙酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到4-(4-methoxyphenyl)-2-phenylquinazoline
  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：

  苯甲酰氯 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 生成 N-(4-methoxybenzyl)-N′-phenylbenzimidamide
  参考文献：
  名称：

  Transition Metal-Free Visible Light-Driven Photoredox Oxidative Annulation of Arylamidines

  摘要：

  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 %).

  DOI：

  10.1021/acs.joc.5b02366

文献信息

• Ph3P/I2-mediated synthesis of N,N′-disubstituted and N,N,N′-trisubstituted amidines
  作者：Wong Phakhodee、Sirilak Wangngae、Nittaya Wiriya、Mookda Pattarawarapan

  DOI：10.1016/j.tetlet.2016.10.069

  日期：2016.11

  A convenient one-pot protocol for the synthesis of N,N′-disubstituted and N,N,N′-trisubstituted amidines is reported. In the presence of the Ph3P–I2/Et3N system, a variety of secondary amides were smoothly reacted with primary or secondary amines to afford the corresponding amidines in good to excellent yields under mild conditions.

  报道了一种方便的一锅法合成N，N'-二取代的N，N，N，N'-三取代的am。在Ph 3 P–I 2 / Et 3 N体系存在下，多种仲酰胺与伯胺或仲胺平稳反应，在温和条件下以良好或极佳的收率得到相应的am。