ethyl 1-benzyl-5-hydroxy-1H-pyrazol-4-carboxylate | 651755-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-benzyl-5-hydroxy-1H-pyrazol-4-carboxylate
• 英文别名: ethyl 1-benzyl-5-hydroxy-1H-pyrazole-4-carboxylate
• CAS: 651755-15-6
• 化学式: C₁₃H₁₄N₂O₃
• mdl: MFCD25289925
• 分子量: 246.266
• InChiKey: HTICYTSSINYVKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.35
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzyl-5-hydroxy-1H-pyrazol-4-carboxylate 在 氢氧化钾 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以59%的产率得到1-苄基-1H-吡唑-5-醇
  参考文献：
  名称：

  New 1-Substituted 4-Cinnamoyl-5- hydroxypyrazoles and Precursors thereof: Synthesis, Ring Closure Reactions and NMR-Spectroscopic Investigations

  摘要：

  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.

  DOI：

  10.3987/com-03-9857
• 作为产物：
  描述：

  苄基肼 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 ethyl 1-benzyl-5-hydroxy-1H-pyrazol-4-carboxylate
  参考文献：
  名称：

  New 1-Substituted 4-Cinnamoyl-5- hydroxypyrazoles and Precursors thereof: Synthesis, Ring Closure Reactions and NMR-Spectroscopic Investigations

  摘要：

  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.

  DOI：

  10.3987/com-03-9857

文献信息

• An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones
  作者：Gernot A Eller、Gytė Vilkauskaitė、Algirdas Šačkus、Vytas Martynaitis、Ashenafi Damtew Mamuye、Vittorio Pace、Wolfgang Holzer

  DOI：10.3762/bjoc.14.110

  日期：——

  transformed into the corresponding 4,4'-bipyrazoles via alkaline hydrolysis and subsequent decarboxylation. Detailed NMR spectroscopic investigations (1H, 13C, 15N) were undertaken with all products prepared. Moreover, the structure of a representative 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylate was confirmed by X-ray crystal structure analysis.

  通过使5-羟基吡唑-4-羧酸酯在回流的亚硫酰氯中反应，可容易地获得5,5'-二氧代-4,4'-联吡唑-4,4'-二羧酸二烷基酯。所获得的二酯可以通过碱水解和随后的脱羧反应转化为相应的4，4′-联吡唑。对所有制备的产物进行了详细的NMR光谱研究（1H，13C，15N）。此外，通过X射线晶体结构分析确认了代表性的5,5'-二氧代-4,4'-联吡唑-4,4'-二羧酸酯的结构。
• Alkoxypyrazoles and the process for their preparation
  申请人：Institut Pasteur

  公开号：EP2151434A1

  公开（公告）日：2010-02-10

  The present invention relates to a process for the preparation of alkoxypyrazoles and new alkoxypyrazole compounds.

  本发明涉及一种制备烷氧基吡唑和新烷氧基吡唑化合物的方法。
• [EN] NEW ALKOXYPYRAZOLES<br/>[FR] NOUVEAUX ALCOXYPYRAZOLES
  申请人：PASTEUR INSTITUT

  公开号：WO2010015656A2

  公开（公告）日：2010-02-11

  The present invention relates to a process for the preparation of alkoxypyrazoles and new alkoxypyrazole compounds.