bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) 2,2'-bipyridine-3,3'-dicarboxylate | 1163299-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) 2,2'-bipyridine-3,3'-dicarboxylate
• CAS: 1163299-19-1
• 化学式: C₃₆H₄₄N₂O₁₄
• 分子量: 728.75
• InChiKey: DCRPCUYPQOBNFR-DSJUORADSA-N

物化性质

• 熔点：
  85-89 °C
• 沸点：
  753.2±60.0 °C(predicted)
• 密度：
  1.273±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  52.0
• 可旋转键数：
  7.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  170.68
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  果糖二丙酮 、 2,2'-联吡啶-3,3'-二羧酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以36%的产率得到bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) 2,2'-bipyridine-3,3'-dicarboxylate
  参考文献：
  名称：

  2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination

  摘要：

  A series of 10 new carbohydrate-substituted bipyridines were prepared from 2,2'-bipyridine-3,3'-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu(II)-catalysed asymmetric electrophilic fluorination of model beta-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.050
• 作为试剂：
  描述：

  2-苄基乙酰乙酸乙酯 在 bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) 2,2'-bipyridine-3,3'-dicarboxylate 、 copper(II) bis(trifluoromethanesulfonate) 、 N-氟代双苯磺酰胺 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到ethyl 2-benzyl-2-fluoro-3-oxobutanoate
  参考文献：
  名称：

  2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination

  摘要：

  A series of 10 new carbohydrate-substituted bipyridines were prepared from 2,2'-bipyridine-3,3'-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu(II)-catalysed asymmetric electrophilic fluorination of model beta-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.050