4-dimethylaminomethyl-1-dimethylaminonaphthalene | 544666-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-dimethylaminomethyl-1-dimethylaminonaphthalene
• 英文别名: 4-[(dimethylamino)methyl]-N,N-dimethylnaphthalen-1-amine
• CAS: 544666-01-5
• 化学式: C₁₅H₂₀N₂
• 分子量: 228.337
• InChiKey: OXQIKGYSOSGNJY-UHFFFAOYSA-N

物化性质

• 沸点：
  323.5±22.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-dimethylaminomethyl-1-dimethylaminonaphthalene 以 水 、 丙酮 为溶剂， 反应 2.0h， 生成 bis-4-(1-N,N-dimethylaminonaphthyl)methane
  参考文献：
  名称：

  摘要：

  Aminomethylation of 1,8-bis(dimethylamino) naphthalene ("proton sponge") afforded a series of its 4-dialkylaminomethyl-substituted derivatives. An attempt to introduce the second peri-dialkylaminomethyl group unexpectedly led to the formation of salts with the 2,2-dialkyl-6,7-bis(dimethylamino)-2-azonia-2,3-dihydrophenalene cation. The structure of one of these salts was established by X-ray diffraction analysis. Treatment of 1,8-bis(dimethylamino)-4-piperidinomethylnaphthale ne with iodomethane gave a spiro compound rather than the expected N-[4,5-bis(dimethylamino)-1-naphthylmethyl]-N-methylpiperidinium iodide. This spiro, compound was generated through cyclodimerization of the 1-naphthylmethyl carbocations. These transformations provide evidence that "proton sponge"-derived Mannich bases quaternized at the dialkylaminomethyl group are unstable and undergo the spontaneous transformation into the resonance-stabilized 4,5-bis(dimethylamino)-1-naphthylmethyl carbocation. By contrast, 4-dialkylamino-1 -dimethylaminomethylnaphthalenes gave methoiodides, which are stable under standard conditions. The latter compounds undergo the nucleophilic substitution of the NR3 group typical of such salts.

  DOI：

  10.1023/a:1022477205623
• 作为产物：
  描述：

  N,N-二甲基-1-萘胺 、 四甲基甲烷二胺 在 溶剂黄146 作用下， 反应 12.0h， 以53%的产率得到4-dimethylaminomethyl-1-dimethylaminonaphthalene
  参考文献：
  名称：

  摘要：

  Aminomethylation of 1,8-bis(dimethylamino) naphthalene ("proton sponge") afforded a series of its 4-dialkylaminomethyl-substituted derivatives. An attempt to introduce the second peri-dialkylaminomethyl group unexpectedly led to the formation of salts with the 2,2-dialkyl-6,7-bis(dimethylamino)-2-azonia-2,3-dihydrophenalene cation. The structure of one of these salts was established by X-ray diffraction analysis. Treatment of 1,8-bis(dimethylamino)-4-piperidinomethylnaphthale ne with iodomethane gave a spiro compound rather than the expected N-[4,5-bis(dimethylamino)-1-naphthylmethyl]-N-methylpiperidinium iodide. This spiro, compound was generated through cyclodimerization of the 1-naphthylmethyl carbocations. These transformations provide evidence that "proton sponge"-derived Mannich bases quaternized at the dialkylaminomethyl group are unstable and undergo the spontaneous transformation into the resonance-stabilized 4,5-bis(dimethylamino)-1-naphthylmethyl carbocation. By contrast, 4-dialkylamino-1 -dimethylaminomethylnaphthalenes gave methoiodides, which are stable under standard conditions. The latter compounds undergo the nucleophilic substitution of the NR3 group typical of such salts.

  DOI：

  10.1023/a:1022477205623