N-(5-(3-tert-butyl-5-formyl-4-hydroxyphenyl)pyridin-2-yl)pivalamide | 1092119-21-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(5-(3-tert-butyl-5-formyl-4-hydroxyphenyl)pyridin-2-yl)pivalamide
• CAS: 1092119-21-5
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: YORAVAWQLPADBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  521.2±50.0 °C(predicted)
• 密度：
  1.153±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79.29
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(5-(3-tert-butyl-5-formyl-4-hydroxyphenyl)pyridin-2-yl)pivalamide 、 (1R,2R)-1,2-diaminocyclohexane 以 四氢呋喃 为溶剂， 以65%的产率得到N,N'-(5,5'-(5,5'-(1E,1'E)-(1R,2R)-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)bis(3-tert-butyl-4-hydroxy-5,1-phenylene))bis(pyridine-5,2-diyl))bis(2,2-dimethylpropanamide)
  参考文献：
  名称：

  Self-Assembled Dinuclear Cobalt(II)-Salen Catalyst Through Hydrogen-Bonding and Its Application to Enantioselective Nitro-Aldol (Henry) Reaction

  摘要：

  Novel chiral dinuclear Co(II)-salen catalysts self-assembled through the pyridone/aminopyridine hydrogen-bonding pair have been developed. The self-assembled dinuclear Co(II)-Salen catalyst results in significant rate acceleration (48 times faster rate) as well, as excellent enantioselectivity (96% ee vs 55% ee) in a nitro-aldol reaction, compared to the corresponding monomeric catalyst. A bimetallic mechanism is suggested by the kinetic experiment showing that the rate taw is second order in [catalyst]. The self-assembly through hydrogen bonding was confirmed by X-ray structure and by the H-1 experiments revealing that the dimerization constant of the novel hydrogen-bonding capable salen (ligand in 25% v/v CD3NO2/CDCl3 is 53 +/- 21 M-1. This result proves the validity of self-assembly based approaches toward the efficient construction of chiral bimetallic catalyst system.

  DOI：

  10.1021/ja807221s
• 作为产物：
  描述：

  N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pivalamide 、 3-叔丁基-2-羟基-5-碘苯甲醛 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以185 mg的产率得到N-(5-(3-tert-butyl-5-formyl-4-hydroxyphenyl)pyridin-2-yl)pivalamide
  参考文献：
  名称：

  Self-Assembled Dinuclear Cobalt(II)-Salen Catalyst Through Hydrogen-Bonding and Its Application to Enantioselective Nitro-Aldol (Henry) Reaction

  摘要：

  Novel chiral dinuclear Co(II)-salen catalysts self-assembled through the pyridone/aminopyridine hydrogen-bonding pair have been developed. The self-assembled dinuclear Co(II)-Salen catalyst results in significant rate acceleration (48 times faster rate) as well, as excellent enantioselectivity (96% ee vs 55% ee) in a nitro-aldol reaction, compared to the corresponding monomeric catalyst. A bimetallic mechanism is suggested by the kinetic experiment showing that the rate taw is second order in [catalyst]. The self-assembly through hydrogen bonding was confirmed by X-ray structure and by the H-1 experiments revealing that the dimerization constant of the novel hydrogen-bonding capable salen (ligand in 25% v/v CD3NO2/CDCl3 is 53 +/- 21 M-1. This result proves the validity of self-assembly based approaches toward the efficient construction of chiral bimetallic catalyst system.

  DOI：

  10.1021/ja807221s