1,4,5-tris(dimethylamino)naphthalene | 199342-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4,5-tris(dimethylamino)naphthalene
• 英文别名: 1,4,5-Naphthalenetriamine, N,N,N',N',N'',N''-hexamethyl-；1-N,1-N,4-N,4-N,5-N,5-N-hexamethylnaphthalene-1,4,5-triamine
• CAS: 199342-43-3
• 化学式: C₁₆H₂₃N₃
• 分子量: 257.379
• InChiKey: WNNRWYQNBICHKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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：
  9.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4,5-tris(dimethylamino)naphthalene 在 tetrafluoroboric acid 作用下， 以 乙醚 为溶剂， 反应 0.03h， 以100%的产率得到1,4,5-tris(dimethylamino)naphthalene hydrotetrafluoroborate
  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：

  6-amino-2,2-dimethyl-2,3-dihydroperimidine 、 碘甲烷 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以55%的产率得到1,4,5-tris(dimethylamino)naphthalene
  参考文献：
  名称：

  摘要：

  Efficient procedures were developed for the two-step synthesis of 1,2,2,3-tetramethyl-2,3-dihydroperimidines and for the one-step synthesis of 1,3-dimethyl-2,3-dihydroperimidines starting from 1,8-diaminonaphthalenes. New possibilities of the use of 2,3-dihydroperimidinium salts in the synthesis of 1,8-bis(dialkylamino) naphthalenes ("proton sponges") containing the IV-isopropyl group along with the A-methyl groups were demonstrated. The 1,1,2,2,3-pentamethyl-2,3-dihydroperimidinium cation exists in the acyclic iminium form responsible for its high reactivity.

  DOI：

  10.1023/a:1011359109826

文献信息

• A Simple and Effective Procedure for theN-Permethylation of Amino-Substituted Naphthalenes
  作者：Vladimir I. Sorokin、Valery A. Ozeryanskii、Alexander F. Pozharskii

  DOI：10.1002/ejoc.200390085

  日期：2003.2

  ohols) with good to excellent yields. Steric hindrance does not prevent the reaction. Some amines with electron-withdrawing groups, especially at nonconjugated positions, are also alkylated. The procedure allows the combination of a reduction (catalytic or by tin dichloride in acidic media) and a methylation in a one-pot process. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  多种氨基取代的萘可以通过 Me2SO4/Na2CO3/H2O（醇）系统进行 N-全甲基化，收率非常好。空间位阻不会阻止反应。一些带有吸电子基团的胺，特别是在非共轭位置，也被烷基化。该程序允许在一锅法中将还原（催化或通过酸性介质中的二氯化锡）和甲基化相结合。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• peri-Naphthylenediamines
  作者：V. A. Ozeryanskii、A. F. Pozharskii

  DOI：10.1007/bf02505681

  日期：1997.8

  Catalytic hydrogenation of 4-nitro-1,8-bis(dimethylamino)naphthalene afforded the previously unknown 1-amino-4,5-bis(dimethylamino)naphthalene subsequent methylation of which gave 1-methylamino and 1-dimethylamino ''proton sponge'' derivatives. The pK(a) values of 1-amino-, 1-methylamino-, and 1-dimethylamino-4,5-bis(dimethylamino)naphthalenes estimated by H-1 NMR in DMSO-d(6) are equal to 9.8, 10.1, and 8.0, respectively.