2-Formyl-6-<(4-methylpiperazin-1-yl)methyl>phenol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Formyl-6-<(4-methylpiperazin-1-yl)methyl>phenol
• 英文别名: 2-formyl-6-((4-methylpiperazin-1-yl)methyl)phenol；2-Hydroxy-3-[(4-methylpiperazin-1-yl)methyl]benzaldehyde
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: TVEBHBWQNDRZDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-氨乙基)吡啶 、 2-Formyl-6-<(4-methylpiperazin-1-yl)methyl>phenol 以 甲醇 为溶剂， 反应 1.0h， 生成 2-(4-Methyl-piperazin-1-ylmethyl)-6-{[(E)-2-pyridin-2-yl-ethylimino]-methyl}-phenol
  参考文献：
  名称：

  A New Method for the Synthesis of Nonsymmetric Dinucleating Ligands by Aminomethylation of Phenols and Salicylaldehydes

  摘要：

  Monoaminomethylated phenols 5-7 and symmetrically diaminomethylated phenols 8 and 9 were prepared in a one-step procedure-from p-cresol, formaldehyde, and a variety of secondary amines by making use of the aromatic Mannich reaction. Nonsymmetric diaminomethylated phenols 10 and 11 were prepared by a sequential aromatic Mannich reaction using p-cresol, formaldehyde, and two different secondary amines. Alternatively, nonsymmetric diaminomethylated phenols 20-24 were prepared by aminomethylation of 5-methylsalicylaldehyde followed by Ca) condensation with a primary amine and subsequent reduction or (b) reductive amination with a secondary amine. Monoami-nomethylated and (non)symmetric diaminomethylated phenols are excellent ligands for the synthesis of mono- and dinuclear transition metal complexes as is illustrated by the isolation of mononuclear iron(III) complex 25 and nonsymmetric dinuclear copper(II) complex 26.

  DOI：

  10.1021/jo00087a046
• 作为产物：
  描述：

  N-甲基哌嗪 、 聚合甲醛 、 水杨醛 以41%的产率得到2-Formyl-6-<(4-methylpiperazin-1-yl)methyl>phenol
  参考文献：
  名称：

  A New Method for the Synthesis of Nonsymmetric Dinucleating Ligands by Aminomethylation of Phenols and Salicylaldehydes

  摘要：

  Monoaminomethylated phenols 5-7 and symmetrically diaminomethylated phenols 8 and 9 were prepared in a one-step procedure-from p-cresol, formaldehyde, and a variety of secondary amines by making use of the aromatic Mannich reaction. Nonsymmetric diaminomethylated phenols 10 and 11 were prepared by a sequential aromatic Mannich reaction using p-cresol, formaldehyde, and two different secondary amines. Alternatively, nonsymmetric diaminomethylated phenols 20-24 were prepared by aminomethylation of 5-methylsalicylaldehyde followed by Ca) condensation with a primary amine and subsequent reduction or (b) reductive amination with a secondary amine. Monoami-nomethylated and (non)symmetric diaminomethylated phenols are excellent ligands for the synthesis of mono- and dinuclear transition metal complexes as is illustrated by the isolation of mononuclear iron(III) complex 25 and nonsymmetric dinuclear copper(II) complex 26.

  DOI：

  10.1021/jo00087a046

文献信息

• Lubben, Marcel; Hage, Ronald; Meetsma, Auke, Inorganic Chemistry, 1995, vol. 34, # 8, p. 2217 - 2224
  作者：Lubben, Marcel、Hage, Ronald、Meetsma, Auke、Bÿma, Koos、Feringa, Ben L.

  DOI：——

  日期：——
• A New Method for the Synthesis of Nonsymmetric Dinucleating Ligands by Aminomethylation of Phenols and Salicylaldehydes
  作者：Marcel Lubben、Ben L. Feringa

  DOI：10.1021/jo00087a046

  日期：1994.4

  Monoaminomethylated phenols 5-7 and symmetrically diaminomethylated phenols 8 and 9 were prepared in a one-step procedure-from p-cresol, formaldehyde, and a variety of secondary amines by making use of the aromatic Mannich reaction. Nonsymmetric diaminomethylated phenols 10 and 11 were prepared by a sequential aromatic Mannich reaction using p-cresol, formaldehyde, and two different secondary amines. Alternatively, nonsymmetric diaminomethylated phenols 20-24 were prepared by aminomethylation of 5-methylsalicylaldehyde followed by Ca) condensation with a primary amine and subsequent reduction or (b) reductive amination with a secondary amine. Monoami-nomethylated and (non)symmetric diaminomethylated phenols are excellent ligands for the synthesis of mono- and dinuclear transition metal complexes as is illustrated by the isolation of mononuclear iron(III) complex 25 and nonsymmetric dinuclear copper(II) complex 26.