4-甲基-6-(5-甲基-1,2-二氢吡唑-3-亚基)环己-2,4-二烯-1-酮 | 20933-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-甲基-6-(5-甲基-1,2-二氢吡唑-3-亚基)环己-2,4-二烯-1-酮
• 英文名称: 3-(2-hydroxy-5-methylphenyl)-5-methylpyrazole
• 英文别名: 4-methyl-2-(5-methyl-1(2)H-pyrazol-3-yl)-phenol；4-Methyl-6-(5-methyl-1,2-dihydro-3H-pyrazol-3-ylidene)cyclohexa-2,4-dien-1-one；4-methyl-2-(5-methyl-1H-pyrazol-3-yl)phenol
• CAS: 20933-37-3
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: PWMFFYRCPZWXHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯-3-硝基吡啶 、 4-甲基-6-(5-甲基-1,2-二氢吡唑-3-亚基)环己-2,4-二烯-1-酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以54%的产率得到2,5-dimethylbenzo[f]pyrazolo[1,5-d]pyrido[3,2-b][1,4]oxazepine
  参考文献：
  名称：

  New tetracyclic 1,4-oxazepines constructed via practically simple tandem condensation strategy from readily available synthons

  摘要：

  A streamlined synthetic methodology towards novel tetracyclic 1,4-oxazepines from readily available precursors is described. The compounds, designed as more soluble version of the earlier described, poorly soluble dibenzo[bf][1,4]oxazepines, were obtained in high yields and as a single regioisomer as a result of three tandem chemical events-nucleophilic aromatic substitution, Smiles rearrangement and denitrocyclization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.026
• 作为产物：
  描述：

  2-羟基-5-甲基苯乙酮 在 sodium 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 4-甲基-6-(5-甲基-1,2-二氢吡唑-3-亚基)环己-2,4-二烯-1-酮
  参考文献：
  名称：

  New tetracyclic 1,4-oxazepines constructed via practically simple tandem condensation strategy from readily available synthons

  摘要：

  A streamlined synthetic methodology towards novel tetracyclic 1,4-oxazepines from readily available precursors is described. The compounds, designed as more soluble version of the earlier described, poorly soluble dibenzo[bf][1,4]oxazepines, were obtained in high yields and as a single regioisomer as a result of three tandem chemical events-nucleophilic aromatic substitution, Smiles rearrangement and denitrocyclization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.026

文献信息

• Wittig; Blumenthal, Chemische Berichte, 1927, vol. 60, p. 1093
  作者：Wittig、Blumenthal

  DOI：——

  日期：——
• Hamed, Ashraf A.; Madkour, Hassan M. F.; Nuaimi, Ibrahim S. Al., Anales de Quimica, 1994, vol. 90, # 5-6, p. 359 - 364
  作者：Hamed, Ashraf A.、Madkour, Hassan M. F.、Nuaimi, Ibrahim S. Al.、Hussain, Badria A.

  DOI：——

  日期：——
• Fitton, Alan O.; Patel, Rajeshkumar N.; Millar, Ross W., Journal of Chemical Research, Miniprint, 1986, # 4, p. 1101 - 1127
  作者：Fitton, Alan O.、Patel, Rajeshkumar N.、Millar, Ross W.

  DOI：——

  日期：——
• Dibenzo[b,f]pyrazolo[1,5-d][1,4]oxazepines: Facile Construction of a Rare Heterocyclic System via Tandem Aromatic Nucleophilic Substitution-Smiles Rearrangement-Denitrocyclization
  作者：Mikhail Krasavin、Alexander Sapegin、Stanislav Kalinin、Alexey Smirnov、Mikhail Dorogov

  DOI：10.1055/s-0031-1289789

  日期：2012.8

  Condensation of 2-(1H-pyrazol-5-yl)phenols with 1-chloro-2-nitrobenzenes under basic conditions in N,N-dimethylformamide results in a tandem, atom-economical, aromatic nucleophilic substitution-Smiles rearrangement-denitrocyclization process to provide pyrazolo-fused dibenzo[b,f][1,4]oxazepines as a single regioisomer.
• Synthesis of new seven-membered benzo-fused heterocyclic ortho-dicarbonitriles
  作者：Zh. V. Chirkova、M. V. Kabanova、S. I. Filimonov、I. G. Abramov

  DOI：10.1134/s1070428015050188

  日期：2015.5

  Methods of the synthesis of new dibenz[b,f]oxepine-2,3-dicarbonitriles and dibenz[b,f]oxazepine-10,11-dicarbonitriles was developed employing as substrates 4-methyl-5-nitrophthalonitrile and 4-bromo-5-nitrophthalonitrile.