5-chloro-4-(dimethylamino)-2-methyl-6-nitro-3(2H)-pyridazinone

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-chloro-4-(dimethylamino)-2-methyl-6-nitro-3(2H)-pyridazinone
• 英文别名: 5-Chloro-4-(dimethylamino)-2-methyl-6-nitropyridazin-3-one
• 化学式: C₇H₉ClN₄O₃
• 分子量: 232.626
• InChiKey: ANGSKYHBHRIAHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二甲胺 、 4,5-dichloro-2-methyl-6-nitro-3(2H)-pyridazinone 以 乙醇 为溶剂， 反应 18.0h， 以41%的产率得到5-chloro-4-(dimethylamino)-2-methyl-6-nitro-3(2H)-pyridazinone
  参考文献：
  名称：

  Lipophilicity of Aminopyridazinone Regioisomers

  摘要：

  Ten pairs of pyridazinone regioisomers were prepared, and their lipophilicity was described by the logarithm of the octanol/water partition coefficient (log P) determined experimentally and calculated with prediction methods. The 4- and 5-(substituted amino)-3(2H)-pyridazinone regioisomers were synthesized by nucleophilic substitution of one of the chloro atoms of 4,5-dichloro-2-methyl-3(2H)pyridazinone or its 6-nitro derivative. Structures of new compounds were proven by spectroscopic methods. The experimental log P values were obtained by a shake flask method in octanol and a Sorensen buffer (pH 7.4) solvent system. A consequent difference was found in the lipophilicity of regioisomers. For each isomer pair, the log P value of the 4-isomer was significantly (average by 0.75 log unit) higher than that of the 5-isomer. Some quantum chemical calculations as well as X-ray analysis of two pairs of regioisomers were also carried out to gain insight into the structural differences of regioisomers. The log P values were calculated by the fragmental approach KOWWIN and a QSPR analysis (3DNET). The a priori KOWWIN gave poor agreement, but with the programs KOWWIN with EVA (experimental value adjusted) and 3DNET, the results were generally in agreement with experiment.

  DOI：

  10.1021/jf0343938

文献信息

• Lipophilicity of Aminopyridazinone Regioisomers
  作者：Massud A. S. Anwair、László Károlyházy、Diána Szabó、Balázs Balogh、István Kövesdi、Veronika Harmat、Judit Krenyácz、Ákos Gellért、Krisztina Takács-Novák、Péter Mátyus

  DOI：10.1021/jf0343938

  日期：2003.8.1

  Ten pairs of pyridazinone regioisomers were prepared, and their lipophilicity was described by the logarithm of the octanol/water partition coefficient (log P) determined experimentally and calculated with prediction methods. The 4- and 5-(substituted amino)-3(2H)-pyridazinone regioisomers were synthesized by nucleophilic substitution of one of the chloro atoms of 4,5-dichloro-2-methyl-3(2H)pyridazinone or its 6-nitro derivative. Structures of new compounds were proven by spectroscopic methods. The experimental log P values were obtained by a shake flask method in octanol and a Sorensen buffer (pH 7.4) solvent system. A consequent difference was found in the lipophilicity of regioisomers. For each isomer pair, the log P value of the 4-isomer was significantly (average by 0.75 log unit) higher than that of the 5-isomer. Some quantum chemical calculations as well as X-ray analysis of two pairs of regioisomers were also carried out to gain insight into the structural differences of regioisomers. The log P values were calculated by the fragmental approach KOWWIN and a QSPR analysis (3DNET). The a priori KOWWIN gave poor agreement, but with the programs KOWWIN with EVA (experimental value adjusted) and 3DNET, the results were generally in agreement with experiment.