3-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridazine | 111961-60-5

• 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-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridazine
• 英文别名: 3-Methyl-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridazin；1,2-Diazabenzocycloheptane, 3-methyl-；3-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridazine
• CAS: 111961-60-5
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: YTNMKCBZFZNUCF-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  325.5±11.0 °C(predicted)
• 密度：
  1.035±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-methyl-2-[(4-methylbenzene)sulfonyl]-2H,4aH,5H,6H,7H,8H,9H-cyclohepta[c]pyridazine 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以43%的产率得到3-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridazine
  参考文献：
  名称：

  From N-sulfonyl,C-homoallyl-hydrazones to pyrazole and pyridazine (N2)-heterocycles: the ultimate aromatization process

  摘要：

  Isomeric six- and five-membered (N-2)-aromatics, 6-methylpyridazines and 5-vinylpyrazoles, which energetic topological aromaticity is comparable to that of benzene, are shown to be efficiently produced by sequential isomerization elimination processes from the corresponding 6-methylidene-1,4,5,6-tetrahydropyridazines and 5-vinylpyrazolines, respectively. The latter precursors are available from the same N-sulfonyl,C-homoallyl-hydrazone substrates by a suitable choice of previously reported conditions for Pd-catalyzed CH-oxidative C,N-ring closing processes. The generality of these cyclization, isomerization, and aromatization reactions, for which detailed mechanisms are proposed, provides a systematic access to wide ranges of 3,4,6-trisubstituted 6-methyl-1,4-dihydropyridazines and 6-methylpyridazines, and their 3,4,5-trisubstituted 5-vinylpyrazole isomers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.005

文献信息

• Levisalles, Bulletin de la Societe Chimique de France, 1957, p. 1009,1011
  作者：Levisalles

  DOI：——

  日期：——
• From N-sulfonyl,C-homoallyl-hydrazones to pyrazole and pyridazine (N2)-heterocycles: the ultimate aromatization process
  作者：Cleve Dionel Mboyi、Carine Duhayon、Yves Canac、Remi Chauvin

  DOI：10.1016/j.tet.2014.05.005

  日期：2014.8

  Isomeric six- and five-membered (N-2)-aromatics, 6-methylpyridazines and 5-vinylpyrazoles, which energetic topological aromaticity is comparable to that of benzene, are shown to be efficiently produced by sequential isomerization elimination processes from the corresponding 6-methylidene-1,4,5,6-tetrahydropyridazines and 5-vinylpyrazolines, respectively. The latter precursors are available from the same N-sulfonyl,C-homoallyl-hydrazone substrates by a suitable choice of previously reported conditions for Pd-catalyzed CH-oxidative C,N-ring closing processes. The generality of these cyclization, isomerization, and aromatization reactions, for which detailed mechanisms are proposed, provides a systematic access to wide ranges of 3,4,6-trisubstituted 6-methyl-1,4-dihydropyridazines and 6-methylpyridazines, and their 3,4,5-trisubstituted 5-vinylpyrazole isomers. (C) 2014 Elsevier Ltd. All rights reserved.