3-Chloro-4-phenethyl-6-p-tolyl-pyridazine | 186449-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-Chloro-4-phenethyl-6-p-tolyl-pyridazine
• 英文别名: 3-Chloro-6-(4-methylphenyl)-4-(2-phenylethyl)pyridazine
• CAS: 186449-58-1
• 化学式: C₁₉H₁₇ClN₂
• 分子量: 308.81
• InChiKey: SGFHVLPRTOEXHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Chloro-4-phenethyl-6-p-tolyl-pyridazine 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以59%的产率得到8-Phenethyl-6-p-tolyl-tetrazolo[1,5-b]pyridazine
  参考文献：
  名称：

  Dehydration of 2-(2-Arylethyl)-2-hydroxy-4-oxopentanoic Acids and their hydrazones to form heterocycles

  摘要：

  Dehydration of 2-(2-arylethyl)-2-hydroxy-4-oxopentanoic acids 1 with hydrochloric acid/acetic acid, affords 3-(2-arylethyl)-5-hydroxy-5-methyl-2(5H)-furanones 4. Compounds of type 1 and 4 represent suitable precursors for the formation of pyridazin-3-ones 7 as they smoothly react with hydrazine. A new series of s-triazolo[4,3-b]pyridazin-3-ones 12 and tetrazolo[1,5-b]pyridazines 15 are obtained from the 3-chloropyridazines 11 upon treatment with semicarbazide and sodium azide, respectively. Reaction of 11 with phenyl- acetyl-hydrazine provides 3-benzyl-6-phenyl-8-(2-phenyl-ethyl)-s-triazolo [4,3-b]pyridazine 13 via dehydrative cyclization of the intermediate 14 which was clarified to exhibit tautomeric equilibria between enol-hydrazine form A and keto-hydrazine form B by means of H-1 and C-13 NMR spectroscopy. Attempts to synthesize 3-alloxy-pyridazines 18 by reacting 11 with sodium alloxide afford N-allyl compounds 17.

  DOI：

  10.1002/prac.19973390104
• 作为产物：
  描述：

  6-(4-methylphenyl)-4-(2-phenylethyl)-2,3-dihydropyridazin-3-one 在 三氯氧磷 作用下， 反应 2.0h， 以71%的产率得到3-Chloro-4-phenethyl-6-p-tolyl-pyridazine
  参考文献：
  名称：

  Dehydration of 2-(2-Arylethyl)-2-hydroxy-4-oxopentanoic Acids and their hydrazones to form heterocycles

  摘要：

  Dehydration of 2-(2-arylethyl)-2-hydroxy-4-oxopentanoic acids 1 with hydrochloric acid/acetic acid, affords 3-(2-arylethyl)-5-hydroxy-5-methyl-2(5H)-furanones 4. Compounds of type 1 and 4 represent suitable precursors for the formation of pyridazin-3-ones 7 as they smoothly react with hydrazine. A new series of s-triazolo[4,3-b]pyridazin-3-ones 12 and tetrazolo[1,5-b]pyridazines 15 are obtained from the 3-chloropyridazines 11 upon treatment with semicarbazide and sodium azide, respectively. Reaction of 11 with phenyl- acetyl-hydrazine provides 3-benzyl-6-phenyl-8-(2-phenyl-ethyl)-s-triazolo [4,3-b]pyridazine 13 via dehydrative cyclization of the intermediate 14 which was clarified to exhibit tautomeric equilibria between enol-hydrazine form A and keto-hydrazine form B by means of H-1 and C-13 NMR spectroscopy. Attempts to synthesize 3-alloxy-pyridazines 18 by reacting 11 with sodium alloxide afford N-allyl compounds 17.

  DOI：

  10.1002/prac.19973390104