4-amino-1-methylamino-5-nitronaphthalene | 1418114-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-amino-1-methylamino-5-nitronaphthalene
• 英文别名: 1-N-methyl-5-nitronaphthalene-1,4-diamine
• CAS: 1418114-56-3
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: GMXOLOZYWCSOJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4,5-bis(dimethylamino)-8-nitronaphthalene-1-yl)phthalimide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 30.0h， 以15%的产率得到4-amino-1-methylamino-5-nitronaphthalene
  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

文献信息

• ‘Proton sponge’ amides: unusual chemistry and conversion into superbasic 6,7-bis(dimethylamino)perimidines
  作者：Valery A. Ozeryanskii、Marina P. Vlasenko、Alexander F. Pozharskii

  DOI：10.1016/j.tet.2012.12.040

  日期：2013.2

  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.