2-<amino>methyl>-6-formyl-4-methylphenol | 155454-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<amino>methyl>-6-formyl-4-methylphenol
• 英文别名: 3-[[Bis(2-pyrrolidin-1-ylethyl)amino]methyl]-2-hydroxy-5-methylbenzaldehyde
• CAS: 155454-69-6
• 化学式: C₂₁H₃₃N₃O₂
• 分子量: 359.512
• InChiKey: UXLWNXLLMOLQNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<amino>methyl>-6-formyl-4-methylphenol 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2-<amino>methyl>-6-<methyl>-4-methylphenol
  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：

  2-(2-Oxo-2-pyrrolidin-1-yl-ethylamino)-1-pyrrolidin-1-yl-ethanone 在 lithium aluminium tetrahydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 29.0h， 生成 2-<amino>methyl>-6-formyl-4-methylphenol
  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

• 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.