4,5-bis(dimethylamino)-1-(p-nitrobenzoylamido)naphthalene | 1418114-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-bis(dimethylamino)-1-(p-nitrobenzoylamido)naphthalene
• 英文别名: N-[4,5-bis(dimethylamino)naphthalen-1-yl]-4-nitrobenzamide
• CAS: 1418114-70-1
• 化学式: C₂₁H₂₂N₄O₃
• 分子量: 378.431
• InChiKey: UKUNBJCNEMRLCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-bis(dimethylamino)-1-(p-nitrobenzoylamido)naphthalene 在 硫酸 、 硝酸 作用下， 反应 0.08h， 以70%的产率得到4,5-bis(dimethylamino)-8-nitro-1-(p-nitrobenzoylamido)naphthalene
  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
• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 1-amino-4,5-bis(dimethylamino)naphthalene 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以50%的产率得到4,5-bis(dimethylamino)-1-(p-nitrobenzoylamido)naphthalene
  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