N,N-bis[2-(6-bromo-4-pyrrolidinopyridinyl)]-p-anisidine | 1408315-38-7

• 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: N,N-bis[2-(6-bromo-4-pyrrolidinopyridinyl)]-p-anisidine
• 英文别名: 6-bromo-N-(6-bromo-4-pyrrolidin-1-ylpyridin-2-yl)-N-(4-methoxyphenyl)-4-pyrrolidin-1-ylpyridin-2-amine
• CAS: 1408315-38-7
• 化学式: C₂₅H₂₇Br₂N₅O
• 分子量: 573.33
• InChiKey: KIMRNBAEBBISEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-bis[2-(6-bromo-4-pyrrolidinopyridinyl)]-p-anisidine 、 2,6-bis(p-anisylamino)-4-pyrrolidinopyridine 在 potassium carbonate 、 copper(I) bromide 作用下， 以 硝基苯 为溶剂， 反应 3.0h， 以96%的产率得到N,N',N"-tris(p-anisyl)azacolix[3](2,6)(4-pyrrolidinopyridine) hydrogen bromide
  参考文献：
  名称：

  Molecular Design of Organic Superbases, Azacalix[3](2,6)pyridines: Catalysts for 1,2- and 1,4-Additions

  摘要：

  The molecular design, characteristics, and catalytic activity of macrocyclic amino compounds, azacalix[3](2,6)pyridine derivatives, were studied. The introduction of an electron-donating group on the pyridine moiety and bridging amino phenyl group enabled the enhancement of the basicity of azacalix[3](2,6)pyridine up to pK(BH+) = 29.5 in CD3CN. These derivatives were shown to be efficient catalysts for 1,4-addition reactions of nitroalkanes or primary alcohols to alpha,beta-unsaturated carbonyl compounds and 1,2-addition reactions of nitroalkanes to aromatic aldehydes.

  DOI：

  10.1021/jo3017428
• 作为产物：
  描述：

  2,6-dibromo-4-pyrrolidinopyridine 、 甲氧苯胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以52%的产率得到N,N-bis[2-(6-bromo-4-pyrrolidinopyridinyl)]-p-anisidine
  参考文献：
  名称：

  Molecular Design of Organic Superbases, Azacalix[3](2,6)pyridines: Catalysts for 1,2- and 1,4-Additions

  摘要：

  The molecular design, characteristics, and catalytic activity of macrocyclic amino compounds, azacalix[3](2,6)pyridine derivatives, were studied. The introduction of an electron-donating group on the pyridine moiety and bridging amino phenyl group enabled the enhancement of the basicity of azacalix[3](2,6)pyridine up to pK(BH+) = 29.5 in CD3CN. These derivatives were shown to be efficient catalysts for 1,4-addition reactions of nitroalkanes or primary alcohols to alpha,beta-unsaturated carbonyl compounds and 1,2-addition reactions of nitroalkanes to aromatic aldehydes.

  DOI：

  10.1021/jo3017428