1-(1-isopropyl-1H-benzimidazol-2-yl)naphthalen-2-ol | 454716-15-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-isopropyl-1H-benzimidazol-2-yl)naphthalen-2-ol
• CAS: 454716-15-5
• 化学式: C₂₀H₁₈N₂O
• 分子量: 302.376
• InChiKey: IHOMTWJNORLTEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  38.05
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(1-isopropyl-1H-benzimidazol-2-yl)naphthalen-2-ol 在 1,2-双(二苯基膦)乙烷氯化镍 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 2-(2-diphenylphosphanyl-naphthalen-1-yl)-isopropyl-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and resolution of 2-(2-diphenylphosphinyl-naphthalen-1-yl)-1-isopropyl-1H-benzoimidazole; a new atropisomeric P,N-chelating ligand for asymmetric catalysis

  摘要：

  A multistep synthesis resulting in a good yield of the title compound 13 (BIMNAP) has been developed based on N,N-acetal-formation and oxidation with MnO2. The product 11 is converted into the corresponding trifluoromethane sulfonate 12 by treatment with (CF3SO2)(2)O followed by a nickel-catalysed coupling-reaction with HPPh2. Resolution of the phosphanamine 13 was carried out via fractional crystallisation of the diastereomeric hexafluorophosphate salts of the Pd-complex 15, formed from reaction of 13 with (+)-di-mu-chlorobis{2-[1-(dimethylamino)ethyl]phenyl-C,N}dipalladium (S)-14. The absolute configurations of the two diastereomers were determined by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00079-4
• 作为产物：
  描述：

  N1-异丙基-1,2-苯二胺 在 manganese(IV) oxide 作用下， 以 甲醇 、 苯 为溶剂， 反应 13.0h， 生成 1-(1-isopropyl-1H-benzimidazol-2-yl)naphthalen-2-ol
  参考文献：
  名称：

  Synthesis and resolution of 2-(2-diphenylphosphinyl-naphthalen-1-yl)-1-isopropyl-1H-benzoimidazole; a new atropisomeric P,N-chelating ligand for asymmetric catalysis

  摘要：

  A multistep synthesis resulting in a good yield of the title compound 13 (BIMNAP) has been developed based on N,N-acetal-formation and oxidation with MnO2. The product 11 is converted into the corresponding trifluoromethane sulfonate 12 by treatment with (CF3SO2)(2)O followed by a nickel-catalysed coupling-reaction with HPPh2. Resolution of the phosphanamine 13 was carried out via fractional crystallisation of the diastereomeric hexafluorophosphate salts of the Pd-complex 15, formed from reaction of 13 with (+)-di-mu-chlorobis{2-[1-(dimethylamino)ethyl]phenyl-C,N}dipalladium (S)-14. The absolute configurations of the two diastereomers were determined by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00079-4