N,N',N''-tris(p-tolyl)azacalix[3](2,6)(4-piperidinopyridine) | 1255773-46-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N',N''-tris(p-tolyl)azacalix[3](2,6)(4-piperidinopyridine)
• 英文别名: 2,8,14-Tris(4-methylphenyl)-5,11,17-tri(piperidin-1-yl)-2,8,14,19,20,21-hexazatetracyclo[13.3.1.13,7.19,13]henicosa-1(18),3,5,7(21),9,11,13(20),15(19),16-nonaene；2,8,14-tris(4-methylphenyl)-5,11,17-tri(piperidin-1-yl)-2,8,14,19,20,21-hexazatetracyclo[13.3.1.13,7.19,13]henicosa-1(18),3,5,7(21),9,11,13(20),15(19),16-nonaene
• CAS: 1255773-46-6
• 化学式: C₅₁H₅₇N₉
• 分子量: 796.074
• InChiKey: SCKMHTGIXXAKNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  60
• 可旋转键数：
  6
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N,N',N''-tris(p-tolyl)azacalix[3](2,6)(4-piperidinopyridine) hydrogen bromide 在 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 生成 N,N',N''-tris(p-tolyl)azacalix[3](2,6)(4-piperidinopyridine)
  参考文献：
  名称：

  Synthesis, Characterization, and Catalytic Reactivity of a Highly Basic Macrotricyclic Aminopyridine

  摘要：

  The synthesis methods, physicochemical and structural characteristics, and catalytic reactivity of new macrocyclic proton chelators, N,N ',N ''-tris(p-tolyl)azacalix[3](2,6)(4-pyrrolidinopyridine) and N,N ',N ''-tris(p-tolyl)azacalix[3](2,6)(4-piperidinopyridine), are studied. The introduction of pyrrolidino and piperidino groups into the pyridine unit enables the enhancement of the synergistic proton affinity of the cavity of the macrotricycle giving a high basicity (pK(BH+) = 28.1 and 27.1 in CD3CN), resulting in a catalytic activity for the Michael addition of nitromethane with alpha,beta-unsaturated carbonyl compounds.

  DOI：

  10.1021/ol102236f

文献信息

• Synthesis, Characterization, and Catalytic Reactivity of a Highly Basic Macrotricyclic Aminopyridine
  作者：Natsuko Uchida、Ayako Taketoshi、Junpei Kuwabara、Toshihide Yamamoto、Yoshiaki Inoue、Yu Watanabe、Takaki Kanbara

  DOI：10.1021/ol102236f

  日期：2010.11.19

  The synthesis methods, physicochemical and structural characteristics, and catalytic reactivity of new macrocyclic proton chelators, N,N ',N ''-tris(p-tolyl)azacalix[3](2,6)(4-pyrrolidinopyridine) and N,N ',N ''-tris(p-tolyl)azacalix[3](2,6)(4-piperidinopyridine), are studied. The introduction of pyrrolidino and piperidino groups into the pyridine unit enables the enhancement of the synergistic proton affinity of the cavity of the macrotricycle giving a high basicity (pK(BH+) = 28.1 and 27.1 in CD3CN), resulting in a catalytic activity for the Michael addition of nitromethane with alpha,beta-unsaturated carbonyl compounds.