2,2'-dinitro-5,5'-(decamethylenedioxy)-1,10-biphenyl | 1041440-61-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2,2'-dinitro-5,5'-(decamethylenedioxy)-1,10-biphenyl
• 英文别名: 5,5-decamethylenedioxy-biphenyl-2,2'-dinitrate；3,22-Dinitro-7,18-dioxatricyclo[17.3.1.12,6]tetracosa-1(22),2,4,6(24),19(23),20-hexaene；3,22-dinitro-7,18-dioxatricyclo[17.3.1.12,6]tetracosa-1(22),2,4,6(24),19(23),20-hexaene
• CAS: 1041440-61-2
• 化学式: C₂₂H₂₆N₂O₆
• 分子量: 414.458
• InChiKey: CINQHKZGUOHILD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2'-dinitro-5,5'-(decamethylenedioxy)-1,10-biphenyl 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以99%的产率得到2,2'-diamino-5,5'-(decamethylenedioxy)-1,10-biphenyl
  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
• 作为产物：
  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

文献信息

• Novel atropisomeric aminophosphine ligands with a bridge across the 5,5′-position of biphenyl for Rh(I)-catalyzed asymmetric hydrogenation
  作者：Hao Wei、Yong Jian Zhang、Yijun Dai、Jiaming Zhang、Wanbin Zhang

  DOI：10.1016/j.tetlet.2008.04.140

  日期：2008.6

  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.
• Synthesis of atropisomeric 5,5′-linked biphenyl bisaminophosphine ligands and their applications in asymmetric catalysis
  作者：Yong Jian Zhang、Hao Wei、Wanbin Zhang

  DOI：10.1016/j.tet.2008.12.056

  日期：2009.2

  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.