2-(4'-dimethylaminophenyl)-pyrimidine-4,6-dicarboxaldehyde bis(2-pyridyl hydrazone) | 1379459-62-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4'-dimethylaminophenyl)-pyrimidine-4,6-dicarboxaldehyde bis(2-pyridyl hydrazone)
• CAS: 1379459-62-7
• 化学式: C₂₄H₂₃N₉
• 分子量: 437.507
• InChiKey: BFEQSUULNSVBOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  103.58
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(4'-dimethylaminophenyl)-pyrimidine-4,6-dicarboxaldehyde bis(2-pyridyl hydrazone) 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到2-(4'-dimethylaminophenyl)-pyrimidine-4,6-dicarboxaldehyde bis(2-pyridyl methyl hydrazone)
  参考文献：
  名称：

  Molecular motion in zinc hydrazone grid complexes

  摘要：

  Four new grid forming hydrazone ligands substituted with methoxy and dimethylamino groups were synthesised. Combination of these ligands with zinc triflate in acetonitrile resulted in self-assembly to form grids as indicated by H-1 NMR and ES-MS. H-1 NMR also showed thermally induced rotation of the intercalated phenyl ring in both the new grids, and in three previously reported grid compounds. Of these seven, five were amenable to study by variable temperature H-1 NMR. Though the observed rates varied by more than an order of magnitude depending upon ligand structure and level of deprotonation, activation energies were similar (similar to 60 kJ/mol) for all complexes studied. This suggests a model in which dissociation of the central pyrimidine ligand precedes phenyl group rotation with an enthalpy of dissociation near zero. The rate of rotation of the phenyl ring increases with an introduction of electron-donating substituents on the phenyl ring, possibly due to an increased repulsion between pi systems.

  DOI：

  10.1080/10610278.2011.593626
• 作为产物：
  描述：

  4-dimethylaminophenylboronic acid ethylene glycol ester 在 selenium(IV) oxide 、 palladium diacetate 、 三苯基膦 、 三氟乙酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 2-(4'-dimethylaminophenyl)-pyrimidine-4,6-dicarboxaldehyde bis(2-pyridyl hydrazone)
  参考文献：
  名称：

  Molecular motion in zinc hydrazone grid complexes

  摘要：

  Four new grid forming hydrazone ligands substituted with methoxy and dimethylamino groups were synthesised. Combination of these ligands with zinc triflate in acetonitrile resulted in self-assembly to form grids as indicated by H-1 NMR and ES-MS. H-1 NMR also showed thermally induced rotation of the intercalated phenyl ring in both the new grids, and in three previously reported grid compounds. Of these seven, five were amenable to study by variable temperature H-1 NMR. Though the observed rates varied by more than an order of magnitude depending upon ligand structure and level of deprotonation, activation energies were similar (similar to 60 kJ/mol) for all complexes studied. This suggests a model in which dissociation of the central pyrimidine ligand precedes phenyl group rotation with an enthalpy of dissociation near zero. The rate of rotation of the phenyl ring increases with an introduction of electron-donating substituents on the phenyl ring, possibly due to an increased repulsion between pi systems.

  DOI：

  10.1080/10610278.2011.593626