1,6-diphenyl-1H-pyrano[2,3-c]pyrazol-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,6-diphenyl-1H-pyrano[2,3-c]pyrazol-4-one
• 英文别名: 1,6-diphenylpyrano[2,3-c]pyrazol-4(1H)-one；1,6-Diphenylpyrano[2,3-c]pyrazol-4-one
• 化学式: C₁₈H₁₂N₂O₂
• 分子量: 288.305
• InChiKey: YPEUIASCQFPKQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-(5-hydroxy-1-phenyl-(1H)-pyrazole-4-yl)-3-phenylprop-2-ene-1-one 在 溴 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 1,6-diphenyl-1H-pyrano[2,3-c]pyrazol-4-one
  参考文献：
  名称：

  Synthesis of some pyrano[2,3-c]pyrazoles

  摘要：

  AbstractSynthetic methods have been developed to prepare pyrano[2,3‐c]pyrazoles with various substituents at ring positions 1, 3, and 6. The 1H‐ and 13C‐NMR properties of these products and their precursors are presented and discussed. J. Heterocyclic Chem., (2011).

  DOI：

  10.1002/jhet.562

文献信息

• A Simple Synthesis of 6-Phenylpyrano[2,3-<i>c</i>]pyrazol-4(1<i>H</i>)-ones
  作者：Wolfgang Holzer、Wilfried Becker、Gernot Eller

  DOI：10.1055/s-2005-872078

  日期：——

  A novel synthesis of substituted 6-phenylpyrano[2,3-c]pyrazol-4(1H)-ones via reaction of various 2-substituted or 2,5-disubstituted 2,4-dihydro-3H-pyrazol-3-ones with phenylpropyn­oyl chloride using calcium hydroxide in refluxing 1,4-dioxane is described. N-Unsubstituted representatives were obtained by treatment of 4-methoxybenzyl-protected congeners with trifluoroacetic acid.

  通过各种2-取代或2,5-二取代的2,4-二氢-3H-吡唑-3-酮与以下反应合成取代的6-苯基吡喃并[2,3-c]吡唑-4(1H)-酮描述了在回流 1,4-二恶烷中使用氢氧化钙的苯丙酰氯。 N-未取代的代表通过用三氟乙酸处理4-甲氧基苄基保护的同源物获得。
• New 1-Substituted 4-Cinnamoyl-5- hydroxypyrazoles and Precursors thereof: Synthesis, Ring Closure Reactions and NMR-Spectroscopic Investigations
  作者：Wolfgang Holzer、Ingrid Krca

  DOI：10.3987/com-03-9857

  日期：——

  Reaction of 1-substituted 5-hydroxy-1H-pyrazoles (pyrazolones) with trans-cinnamoyl chloride/calcium hydroxide in dioxane affords the corresponding 4-cinnamoyl-5-hydroxy-1H-pyrazoles. Cyclization of the latter into 5,6-dihydropyrano[2,3-c]pyrazol-4-ones proceeds in very low yields upon treatment with concentrated sulfuric acid. 1,6-Diphenyl-1H-pyrano[2,3-c]pyrazol-4-one was synthesized by reaction of of 4-acetyl-5-hydroxy-1-phenyl-1H-pyrazole with benzoyl chloride and lithium bis(trimethylsilyl)amide and subsequent cyclization of the thus obtained 1,3-diketone. NMR-spectroscopic investigations with the obtained 4-substituted 5-hydroxypyrazoles and their precursors regarding their tautomeric behavior in various solvents are presented.