1,8-bis(dimethylamino)-4-piperidinomethylnaphthalene | 544665-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,8-bis(dimethylamino)-4-piperidinomethylnaphthalene
• 英文别名: 1-N,1-N,8-N,8-N-tetramethyl-4-(piperidin-1-ylmethyl)naphthalene-1,8-diamine
• CAS: 544665-87-4
• 化学式: C₂₀H₂₉N₃
• 分子量: 311.47
• InChiKey: FCZJARCEHNOCOB-UHFFFAOYSA-N

物化性质

• 沸点：
  421.2±40.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,8-bis(dimethylamino)-4-piperidinomethylnaphthalene 在 碘甲烷 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以93 mg的产率得到
  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：

  哌啶 、 聚合甲醛 、 1,8-双二甲氨基萘 在 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 36.0h， 以86%的产率得到1,8-bis(dimethylamino)-4-piperidinomethylnaphthalene
  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