N-benzyl-N'-phenylpivalimidamide | 208585-32-4

• 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-N'-phenylpivalimidamide
• 英文别名: N-benzyl-N′-phenylpivalimidamide；N'-benzyl-2,2-dimethyl-N-phenylpropanimidamide
• CAS: 208585-32-4
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: BTDHOWOFNFQLHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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-N'-phenylpivalimidamide 在 碘苯二乙酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以76%的产率得到2-tert-butyl-4-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：

  N-benzyl-2,2-dimethylpropanamide 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-N'-phenylpivalimidamide
  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

• Electron Transfer Chain Reactions in the Alkylation of Isonitriles by Alkylmercury Halides.
  作者：Glen A. Russell、Ragine Rajaratnam、Ping Chen、Olle Matsson、Jadwiga Trocha-Grimshaw、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0528

  日期：——

  Imidoyl (PhN=CR.) or acyl (RCO.) radicals undergo electron transfer to alkylmercury halides in Me2SO or PhH solution. Addition of t-Bu-. or i-Pr-. to isonitriles followed by electron transfer forms the nitrilium ion which is converted into the amide in Me2SO; into the imidoyl halide in PhH, and into the amidine in PhH solution containing primary or secondary amines.
• 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 %).