5-dimethylamino-4-methylaminonaphthalene-1,2-dione | 1418114-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-dimethylamino-4-methylaminonaphthalene-1,2-dione
• CAS: 1418114-45-0
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: FCEFJQLEQFABRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  在 硝酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.17h， 以2%的产率得到5-dimethylamino-4-methylaminonaphthalene-1,2-dione
  参考文献：
  名称：

  ‘Proton sponge’ amides: unusual chemistry and conversion into superbasic 6,7-bis(dimethylamino)perimidines

  摘要：

  Starting from 1-acylamino-4,5-bis(dimethylamino)naphthalenes, the first representatives of previously unknown 6,7-bis(dimethylamino)perimidines have been synthesized. In accordance with the electron-donor nature of the heterocyclic rings in these compounds they behave as proton sponges, displaying higher basicity (pK(a) 8.4-93, DMSO) than those of the parent proton sponge (pK(a) 7.5, DMSO; 18.6, MeCN) and perimidine (pK(a) 13.6, MeCN). In accord with OFT calculations and proton transfer experiments, 1H-6,7-bis(dimethylamino)perimidines have been shown to exist as neutral rather than zwitterionic tautomers. A number of interesting observations concerning structure, synthesis, and reactivity of 1-acylamino-4,5-bis(dimethylamino)-8-nitronaphthalenes have been made. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.040