1,3-dimethyl-6-nitroperimidin-2(1H)-one | 58629-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-dimethyl-6-nitroperimidin-2(1H)-one
• 英文别名: 1,3-dimethyl-6-nitroperimidone；6-Nitro-1,3-dimethylperimidon；1,3-dimethyl-6-nitro-1H,3H-perimidin-2-one；1,3-dimethyl-6-nitroperimidin-2-one
• CAS: 58629-42-8
• 化学式: C₁₃H₁₁N₃O₃
• 分子量: 257.249
• InChiKey: ZFWVILFVKGVBNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-6-nitroperimidin-2(1H)-one 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 以54%的产率得到1,3-dimethyl-6,7-dinitro-1H-perimiden-2-one
  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：

  1,3-dimethyl-1H-perimidin-2(3H)-one 在 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以84%的产率得到1,3-dimethyl-6-nitroperimidin-2(1H)-one
  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

• BOROVLEV I. V.; POZHARSKIJ A. F.; KOROLEVA V. N., XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1976, HO 12, 1692-1695
  作者：BOROVLEV I. V.、 POZHARSKIJ A. F.、 KOROLEVA V. N.

  DOI：——

  日期：——
• Pozharskii; Ozeryanskii; Kuz'menko, Russian Journal of Organic Chemistry, 1996, vol. 32, # 1, p. 66 - 72
  作者：Pozharskii、Ozeryanskii、Kuz'menko

  DOI：——

  日期：——