5,5'-dihydroxy-2,2'-dinitrobiphenyl | 122828-96-0

• 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: 5,5'-dihydroxy-2,2'-dinitrobiphenyl
• 英文别名: 3-(5-Hydroxy-2-nitrophenyl)-4-nitrophenol
• CAS: 122828-96-0
• 化学式: C₁₂H₈N₂O₆
• 分子量: 276.205
• InChiKey: PBVJHOCVQZHADE-UHFFFAOYSA-N

物化性质

• 熔点：
  214-215 °C
• 沸点：
  568.5±50.0 °C(predicted)
• 密度：
  1.575±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5'-dihydroxy-2,2'-dinitrobiphenyl 、 1,10-二溴癸烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 以55%的产率得到2,2'-dinitro-5,5'-(decamethylenedioxy)-1,10-biphenyl
  参考文献：
  名称：

  Synthesis of atropisomeric 5,5′-linked biphenyl bisaminophosphine ligands and their applications in asymmetric catalysis

  摘要：

  Atropisomeric 5,5'-linked biphenyl bisaminophosphine ligands 2 has been synthesized. The axial chirality of this type of ligands can be retained by macro ring strain produced from 5,5'-linkage of biphenyl even without 6,6'-substituents on biphenyls. The Rh complex of bisaminophosphine 2a as a catalyst is effectively working in the asymmetric hydrogenation of methyl (Z)-2-acetamido-3-arylacrylates, however, for hydrogenation of arylenamide, the low enantioselectivity was observed. When the ligands applied to Pd-catalyzed allylic alkylation, it is found that ligand 2b having a longer backbone linkage is a better ligand for enantioselection in the reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.056
• 作为产物：
  描述：

  5,5'-dimethoxy-2,2'-dinitrobiphenyl 在 三氯化铝 、 十二硫醇 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到5,5'-dihydroxy-2,2'-dinitrobiphenyl
  参考文献：
  名称：

  Novel atropisomeric aminophosphine ligands with a bridge across the 5,5′-position of biphenyl for Rh(I)-catalyzed asymmetric hydrogenation

  摘要：

  A new type of atropisomeric bisaminophosphine ligands 2 with a bridge across the 5,5'-position of biphenyl has been developed. The axial chirality of this type of ligands can be retained by macro-ring strain produced from 5,5'-linkage of biphenyl even without 6,6'-substituents on biphenyls. The ligand (R)-2a showed high catalytic activities and enantioselectivities (up to 95.3% ee and quantitative yields) for Rh(I)-catalyzed asymmetric hydrogenation of a variety of methyl (Z)-2-acetamido-3-arylacrylates, (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.140