N-benzoyl-N'-n-butylbenzamidine

• 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-benzoyl-N'-n-butylbenzamidine
• 英文别名: N-(N-butyl-C-phenylcarbonimidoyl)benzamide
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: RHTRNDPKNLRJPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-butylbenzimidamide 、 苯甲酰氯 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 1.5h， 以88%的产率得到N-benzoyl-N'-n-butylbenzamidine
  参考文献：
  名称：

  N-Acylamidine Palladium(II) Complexes. Synthesis, Structures, and Catalytic Activity for Suzuki−Miyaura Cross-Coupling Reactions:  Experiments and DFT Calculations

  摘要：

  N-Acylamidines 2 are easily prepared by acylation of amidines 1. Upon treatment with PdCl2(PhCN)(2), they form 2:1 PdCl2 complexes 3 with trans configuration, acting as monodentate ligands via the nitrogen atom remote from the carbonyl group. The structures of the complexes 3a-c in the solid state were obtained by X-ray crystallography. As studied by DFT calculations on 2:1 model complexes, many isomeric structures 6 with different conformations and configurations are associated with local minima on the energy hyperface within an energy range of 4 kcal/mol. The complexes 3 show very high catalytic activity in Suzuki-Miyaura cross-coupling reactions, either as isolated crystals or prepared in situ without isolation.

  DOI：

  10.1021/jo034455t

文献信息

• <i>N-</i>Acylamidine Palladium(II) Complexes. Synthesis, Structures, and Catalytic Activity for Suzuki−Miyaura Cross-Coupling Reactions:  Experiments and DFT Calculations
  作者：Jan K. Eberhardt、Roland Fröhlich、Ernst-Ulrich Würthwein

  DOI：10.1021/jo034455t

  日期：2003.8.1

  N-Acylamidines 2 are easily prepared by acylation of amidines 1. Upon treatment with PdCl2(PhCN)(2), they form 2:1 PdCl2 complexes 3 with trans configuration, acting as monodentate ligands via the nitrogen atom remote from the carbonyl group. The structures of the complexes 3a-c in the solid state were obtained by X-ray crystallography. As studied by DFT calculations on 2:1 model complexes, many isomeric structures 6 with different conformations and configurations are associated with local minima on the energy hyperface within an energy range of 4 kcal/mol. The complexes 3 show very high catalytic activity in Suzuki-Miyaura cross-coupling reactions, either as isolated crystals or prepared in situ without isolation.