1-N,4-N-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-2,5-bis(prop-2-enoxy)benzene-1,4-dicarboxamide | 214205-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-N,4-N-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-2,5-bis(prop-2-enoxy)benzene-1,4-dicarboxamide
• CAS: 214205-86-4
• 化学式: C₃₂H₃₂N₂O₆
• 分子量: 540.616
• InChiKey: WJCPOLRAPXSMRP-HHGOQMMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-N,4-N-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-2,5-bis(prop-2-enoxy)benzene-1,4-dicarboxamide 在 sodium tetrahydroborate 、 四(三苯基膦)钯 作用下， 以 乙醚 为溶剂， 反应 14.0h， 以93%的产率得到2,5-dihydroxy-1-N,4-N-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]benzene-1,4-dicarboxamide
  参考文献：
  名称：

  Chiral Benzoquinones as a New Class of Ligands for Asymmetric Catalysis:  Synthesis and Application to the Palladium(II)-Catalyzed 1,4-Dialkoxylation of 1,3-Dienes

  摘要：

  Chiral C-2-symmetric 2,5-bisamide hydroquinone ligands, with beta-amino alcohols as chiral building units, were synthesized in excellent overall yields. The ligands gave up to 54.4% ee in the palladium-catalyzed 1,4-dialkoxylation of 1,3-dienes. These findings demonstrate the potential of asymmetric induction utilizing chiral benzoquinones as ligands in palladium(II) catalysis, albeit with modest enantiomeric excesses. Weakly coordinating hydroxyl groups of the ligand appear to be crucial for the success of the reaction. Mechanistic aspects and the origin of enantioselectivity are also discussed.

  DOI：

  10.1021/jo980561x
• 作为产物：
  描述：

  2,5-二羟基对苯二甲酸乙酯 在 lithium hydroxide 、 氯化亚砜 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 1-N,4-N-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-2,5-bis(prop-2-enoxy)benzene-1,4-dicarboxamide
  参考文献：
  名称：

  Chiral Benzoquinones as a New Class of Ligands for Asymmetric Catalysis:  Synthesis and Application to the Palladium(II)-Catalyzed 1,4-Dialkoxylation of 1,3-Dienes

  摘要：

  Chiral C-2-symmetric 2,5-bisamide hydroquinone ligands, with beta-amino alcohols as chiral building units, were synthesized in excellent overall yields. The ligands gave up to 54.4% ee in the palladium-catalyzed 1,4-dialkoxylation of 1,3-dienes. These findings demonstrate the potential of asymmetric induction utilizing chiral benzoquinones as ligands in palladium(II) catalysis, albeit with modest enantiomeric excesses. Weakly coordinating hydroxyl groups of the ligand appear to be crucial for the success of the reaction. Mechanistic aspects and the origin of enantioselectivity are also discussed.

  DOI：

  10.1021/jo980561x

文献信息

• Chiral Benzoquinones as a New Class of Ligands for Asymmetric Catalysis:  Synthesis and Application to the Palladium(II)-Catalyzed 1,4-Dialkoxylation of 1,3-Dienes
  作者：Kenichiro Itami、Andreas Palmgren、Atli Thorarensen、Jan-E. Bäckvall

  DOI：10.1021/jo980561x

  日期：1998.9.1

  Chiral C-2-symmetric 2,5-bisamide hydroquinone ligands, with beta-amino alcohols as chiral building units, were synthesized in excellent overall yields. The ligands gave up to 54.4% ee in the palladium-catalyzed 1,4-dialkoxylation of 1,3-dienes. These findings demonstrate the potential of asymmetric induction utilizing chiral benzoquinones as ligands in palladium(II) catalysis, albeit with modest enantiomeric excesses. Weakly coordinating hydroxyl groups of the ligand appear to be crucial for the success of the reaction. Mechanistic aspects and the origin of enantioselectivity are also discussed.