4,4'-(2,2'-dihydroxybiphenyl-3,3'-diyl)bis(N2,N6-bis(2-((S)-4-methyl-4,5-dihydrooxazol-2-yl)phenyl)pyridine-2,6-dicarboxamide) | 1037078-43-5

• 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: 4,4'-(2,2'-dihydroxybiphenyl-3,3'-diyl)bis(N2,N6-bis(2-((S)-4-methyl-4,5-dihydrooxazol-2-yl)phenyl)pyridine-2,6-dicarboxamide)
• CAS: 1037078-43-5
• 化学式: C₆₆H₅₆N₁₀O₁₀
• 分子量: 1149.23
• InChiKey: QGIGZZVBSRMKRX-ZQWQDMLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.56
• 重原子数：
  86.0
• 可旋转键数：
  15.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  269.0
• 氢给体数：
  6.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  4,4'-(2,2'-dihydroxybiphenyl-3,3'-diyl)bis(N2,N6-bis(2-((S)-4-methyl-4,5-dihydrooxazol-2-yl)phenyl)pyridine-2,6-dicarboxamide) 、 二苯基氯化膦 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以61%的产率得到4,4'-(2,2'-bis(diphenylphosphinooxy)biphenyl-3,3'-diyl)bis(N2,N6-bis(2-((S)-4-methyl-4,5-dihydrooxazol-2-yl)phenyl)pyridine-2,6-dicarboxamide)
  参考文献：
  名称：

  Conformationally Driven Asymmetric Induction of a Catalytic Dendrimer

  摘要：

  Nature's catalysts promote the reactions necessary for life with extremely high specificity by folding into specific shapes capable of communicating remote structural information to an active site. Achieving this objective in synthetic systems has been hampered by the lack of information concerning how dynamic conformational chirality can influence the stereoselectivity of a catalytic process. Herein, we report the first illustration of a catalytic dendrimer that achieves high enantioselectivity by amplifying/propagating local chirality via a dynamically folded structure. Experimental evidence supports a chiral relay mechanism that propagates local terminal chirality of the dendron to the axial chirality of the biphenyl core through the helical secondary structure of the dendron.

  DOI：

  10.1021/ja802308a
• 作为产物：
  描述：

  4,4'-(2,2'-bis(benzyloxy)biphenyl-3,3'-diyl)bis(N2,N6-bis(2-((S)-4-methyl-4,5-dihydrooxazol-2-yl)phenyl)pyridine-2,6-dicarboxamide) 在 10% Pd/C 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.0h， 以64%的产率得到4,4'-(2,2'-dihydroxybiphenyl-3,3'-diyl)bis(N2,N6-bis(2-((S)-4-methyl-4,5-dihydrooxazol-2-yl)phenyl)pyridine-2,6-dicarboxamide)
  参考文献：
  名称：

  Conformationally Driven Asymmetric Induction of a Catalytic Dendrimer

  摘要：

  Nature's catalysts promote the reactions necessary for life with extremely high specificity by folding into specific shapes capable of communicating remote structural information to an active site. Achieving this objective in synthetic systems has been hampered by the lack of information concerning how dynamic conformational chirality can influence the stereoselectivity of a catalytic process. Herein, we report the first illustration of a catalytic dendrimer that achieves high enantioselectivity by amplifying/propagating local chirality via a dynamically folded structure. Experimental evidence supports a chiral relay mechanism that propagates local terminal chirality of the dendron to the axial chirality of the biphenyl core through the helical secondary structure of the dendron.

  DOI：

  10.1021/ja802308a