ethyl 3-(3-benzyloxy-4-methoxyphenyl)-4-(1H-pyrrol-1-yl)-1H-pyrazole-5-carboxylate | 757189-08-5

• 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 3-(3-benzyloxy-4-methoxyphenyl)-4-(1H-pyrrol-1-yl)-1H-pyrazole-5-carboxylate
• CAS: 757189-08-5
• 化学式: C₂₄H₂₃N₃O₄
• 分子量: 417.464
• InChiKey: IYNBQSXCKGGWJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78.37
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(3-benzyloxy-4-methoxyphenyl)-4-(1H-pyrrol-1-yl)-1H-pyrazole-5-carboxylate 在 氢溴酸 、 sodium hydride 、 三氯氧磷 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 3-(3-hydroxy-4-methoxyphenyl)-1-methylpyrazolo[3,4-b]pyrrolizin-8(1H)-one
  参考文献：
  名称：

  Synthesis of Novel Pyrazolopyrrolizinones as Prospective Anticancer Agents

  摘要：

  Herein we describe the access of novel pyrazolopyrrolizinones from commercial arylacetonitriles. The first step conducts to the corresponding aminoester which was first submitted to Clauson-Kaas procedure. Amidification and cyclisation afford then the first examples of the expected heterocycles. In order to improve the sequence and to obtain N-substituted isomers, 3-aryl-5-(pyrrolidin-1-ylcarbonyl)-4-(1H-pyrrol-1-yl)-1H-pyrazoles (5) were alkylated and conduct to two different N-substituted pyrazoles. These novel products were separated by chromatography and clearly identified using different analytical techniques. Application of the cyclisation procedure conducts then to the two corresponding final title products.

  DOI：

  10.3987/com-06-10824
• 作为产物：
  描述：

  (3-苄氧基-4-甲氧基苯基)-乙腈 在 sodium ethanolate 、 4-氯吡啶盐酸盐 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.25h， 生成 ethyl 3-(3-benzyloxy-4-methoxyphenyl)-4-(1H-pyrrol-1-yl)-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  Synthesis of Novel Pyrazolopyrrolizinones as Prospective Anticancer Agents

  摘要：

  Herein we describe the access of novel pyrazolopyrrolizinones from commercial arylacetonitriles. The first step conducts to the corresponding aminoester which was first submitted to Clauson-Kaas procedure. Amidification and cyclisation afford then the first examples of the expected heterocycles. In order to improve the sequence and to obtain N-substituted isomers, 3-aryl-5-(pyrrolidin-1-ylcarbonyl)-4-(1H-pyrrol-1-yl)-1H-pyrazoles (5) were alkylated and conduct to two different N-substituted pyrazoles. These novel products were separated by chromatography and clearly identified using different analytical techniques. Application of the cyclisation procedure conducts then to the two corresponding final title products.

  DOI：

  10.3987/com-06-10824

文献信息

• First synthesis of arylpyrrolo- and pyrazolopyrrolizinones as useful agents with potential biological interest
  作者：Christophe Rochais、Vincent Lisowski、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.tetlet.2004.06.047

  日期：2004.8

  three or four steps starting from aminoarylpyrrole and pyrazole carboxylates through the cyclisation of a Vilsmeier–Haack intermediate. This synthesis was enhanced by diverse N-protections of the aza-heterocycle and furnish new series with potential biological interest.

  新型芳基吡咯并吡咯并吡咯并吡嗪酮是通过三步或四步制备的，从氨基芳基吡咯和吡唑羧酸酯开始，通过Vilsmeier-Haack中间体的环化反应。通过氮杂杂环的各种N-保护增强了该合成，并提供了具有潜在生物学意义的新系列。