2,2'-dinitro-5,5'-(octamethylenedioxy)-1,10-biphenyl | 1025772-71-7

• 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'-(octamethylenedioxy)-1,10-biphenyl
• 英文别名: 3,20-Dinitro-7,16-dioxatricyclo[15.3.1.12,6]docosa-1(20),2,4,6(22),17(21),18-hexaene；3,20-dinitro-7,16-dioxatricyclo[15.3.1.12,6]docosa-1(20),2,4,6(22),17(21),18-hexaene
• CAS: 1025772-71-7
• 化学式: C₂₀H₂₂N₂O₆
• 分子量: 386.404
• InChiKey: YNBWTKSOUPHKFP-UHFFFAOYSA-N

物化性质

• 熔点：
  192-196 °C
• 沸点：
  588.4±43.0 °C(predicted)
• 密度：
  1.231±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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'-(octamethylenedioxy)-1,10-biphenyl 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以100%的产率得到2,2'-diamino-5,5'-(octamethylenedioxy)-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 、 1,8-二溴辛烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到2,2'-dinitro-5,5'-(octamethylenedioxy)-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

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.