3-tert-butyl-2-hydroxy-5-((6-oxo-1,6-dihydropyridin-2-yl)ethynyl)benzaldehyde | 1092119-19-1

• 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: 3-tert-butyl-2-hydroxy-5-((6-oxo-1,6-dihydropyridin-2-yl)ethynyl)benzaldehyde
• CAS: 1092119-19-1
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: VGKVLXVNWVOIDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70.16
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-tert-butyl-2-hydroxy-5-((6-oxo-1,6-dihydropyridin-2-yl)ethynyl)benzaldehyde 、 (1R,2R)-1,2-diaminocyclohexane 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到6,6'-(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(ethyne-2,1-diyl))dipyridin-2(1H)-one
  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：

  5-((6-(benzyloxy)pyridin-2-yl)ethynyl)-3-tert-butyl-2-hydroxybenzaldehyde 在 三甲基硅咪唑 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到3-tert-butyl-2-hydroxy-5-((6-oxo-1,6-dihydropyridin-2-yl)ethynyl)benzaldehyde
  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