3-methyl-6-(naphthalen-2-yl)pyridazine | 68206-13-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-methyl-6-(naphthalen-2-yl)pyridazine
• 英文别名: 3-Methyl-6-naphthalen-2-ylpyridazine；3-methyl-6-naphthalen-2-ylpyridazine
• CAS: 68206-13-3
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: RVMYHWNRSLWHTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1-(naphthalen-2-yl)-2-tosylethan-1-one 在 indium(III) triflate 、 hydrazine hydrate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 4.0h， 生成 3-methyl-6-(naphthalen-2-yl)pyridazine
  参考文献：
  名称：

  In(OTf)3-mediated synthesis of substituted pyridazines

  摘要：

  In(OTf)(3) (4c)-mediated one-pot (4+2) cyclocondensation of gamma-alkynones 3 with N2H4(aq) in dioxane affords substituted pyridazines 5 in good yields via a sequential desulfonative or dehydrogenative aromatization. The facile transformation proceeds by a facile synthetic sequence starting with an alpha-propargylation of beta-ketosulfones 1 and a cyclocondensation of gamma-alkynones 3 with N2H4(aq). The method provides a mild and efficient condition. Moreover, this route can be enlarged to multigram scale. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.025

文献信息

• 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.
• In(OTf)3-mediated synthesis of substituted pyridazines
  作者：Meng-Yang Chang、Yi-Ju Lu、Yu-Chieh Cheng

  DOI：10.1016/j.tet.2015.07.025

  日期：2015.9

  In(OTf)(3) (4c)-mediated one-pot (4+2) cyclocondensation of gamma-alkynones 3 with N2H4(aq) in dioxane affords substituted pyridazines 5 in good yields via a sequential desulfonative or dehydrogenative aromatization. The facile transformation proceeds by a facile synthetic sequence starting with an alpha-propargylation of beta-ketosulfones 1 and a cyclocondensation of gamma-alkynones 3 with N2H4(aq). The method provides a mild and efficient condition. Moreover, this route can be enlarged to multigram scale. (C) 2015 Elsevier Ltd. All rights reserved.