1-amino-4,5,8-tris(dimethylamino)naphthalene | 496925-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-amino-4,5,8-tris(dimethylamino)naphthalene
• 英文别名: 1-N,1-N,4-N,4-N,5-N,5-N-hexamethylnaphthalene-1,4,5,8-tetramine
• CAS: 496925-18-9
• 化学式: C₁₆H₂₄N₄
• 分子量: 272.393
• InChiKey: AVYCMSGYROFRRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-amino-4,5,8-tris(dimethylamino)naphthalene 在 tetrafluoroboric acid 、 sodium carbonate 作用下， 以 乙醚 、 水 为溶剂， 反应 10.03h， 生成 1,4,5,8-tetrakis(dimethylamino)naphthalene bis(tetrafluoroborate)
  参考文献：
  名称：

  萘二甲胺：XXXIV。1,4,5,8-四（二甲基氨基）萘：合成的替代方法

  摘要：

  New methods were proposed for synthesizing 1,4,5,8-tetrakis(dimethylamino)naphthalene with an overall yield of 4 to 12% to replace the known procedure ensuring an overall yield of 2%. Catalytic hydrogenation was shown to be inapplicable for preparation of polyaminonaphthalenes from nitro compounds having 3 or 4 nitro gruops in the alpha-positions. Nucleophilic amination of 1,5-dinitronaphthalene in the system NH2OH/NaOH/MeOH yields 1-amino-4-nitronaphthalene. The nitration of 1,5-bis(p-tolylsulfonylamino)naphthalene leads to formation of 2,6-dinitro rather than 4,8-dinitro derivative, as it was believed formerly. This was confirmed by transformation of the latter into 1,2,5,6-tetrakis(dimethylamino)naphthalene. 3-Nitro, 2,6-dinitro, 2,6-diamino, and 2,4,6,8-tetranitro derivatives of 1,5-bis(dimethylamino)naphthalene, nitro and amino derivatives of 1,4,5-tris(dimethylamino)naphthalene, and 4,5-diamino-1,8-bis(methylamino)naphthalene were synthesized. By treatment with perchloric acid 1,4,5,8-tetrakis(dimethylamino)naphthalene was oxidized to 2,3-dihydroperimidinium salt.

  DOI：

  10.1023/a:1019615206870
• 作为产物：
  描述：

  1,4,5-tris(dimethylamino)-8-nitronaphthalene 在 tin(ll) chloride 作用下， 以 盐酸 、 乙醇 为溶剂， 反应 1.0h， 以80%的产率得到1-amino-4,5,8-tris(dimethylamino)naphthalene
  参考文献：
  名称：

  萘二甲胺：XXXIV。1,4,5,8-四（二甲基氨基）萘：合成的替代方法

  摘要：

  New methods were proposed for synthesizing 1,4,5,8-tetrakis(dimethylamino)naphthalene with an overall yield of 4 to 12% to replace the known procedure ensuring an overall yield of 2%. Catalytic hydrogenation was shown to be inapplicable for preparation of polyaminonaphthalenes from nitro compounds having 3 or 4 nitro gruops in the alpha-positions. Nucleophilic amination of 1,5-dinitronaphthalene in the system NH2OH/NaOH/MeOH yields 1-amino-4-nitronaphthalene. The nitration of 1,5-bis(p-tolylsulfonylamino)naphthalene leads to formation of 2,6-dinitro rather than 4,8-dinitro derivative, as it was believed formerly. This was confirmed by transformation of the latter into 1,2,5,6-tetrakis(dimethylamino)naphthalene. 3-Nitro, 2,6-dinitro, 2,6-diamino, and 2,4,6,8-tetranitro derivatives of 1,5-bis(dimethylamino)naphthalene, nitro and amino derivatives of 1,4,5-tris(dimethylamino)naphthalene, and 4,5-diamino-1,8-bis(methylamino)naphthalene were synthesized. By treatment with perchloric acid 1,4,5,8-tetrakis(dimethylamino)naphthalene was oxidized to 2,3-dihydroperimidinium salt.

  DOI：

  10.1023/a:1019615206870

文献信息

• ——
  作者：V. I. Sorokin、V. A. Ozeryanskii、A. F. Pozharskii

  DOI：10.1023/a:1019615206870

  日期：——

  New methods were proposed for synthesizing 1,4,5,8-tetrakis(dimethylamino)naphthalene with an overall yield of 4 to 12% to replace the known procedure ensuring an overall yield of 2%. Catalytic hydrogenation was shown to be inapplicable for preparation of polyaminonaphthalenes from nitro compounds having 3 or 4 nitro gruops in the alpha-positions. Nucleophilic amination of 1,5-dinitronaphthalene in the system NH2OH/NaOH/MeOH yields 1-amino-4-nitronaphthalene. The nitration of 1,5-bis(p-tolylsulfonylamino)naphthalene leads to formation of 2,6-dinitro rather than 4,8-dinitro derivative, as it was believed formerly. This was confirmed by transformation of the latter into 1,2,5,6-tetrakis(dimethylamino)naphthalene. 3-Nitro, 2,6-dinitro, 2,6-diamino, and 2,4,6,8-tetranitro derivatives of 1,5-bis(dimethylamino)naphthalene, nitro and amino derivatives of 1,4,5-tris(dimethylamino)naphthalene, and 4,5-diamino-1,8-bis(methylamino)naphthalene were synthesized. By treatment with perchloric acid 1,4,5,8-tetrakis(dimethylamino)naphthalene was oxidized to 2,3-dihydroperimidinium salt.