1-(4,5-dihydropyrazol-1-yl)but-2-en-1-one | 900188-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 1-(4,5-dihydropyrazol-1-yl)but-2-en-1-one
• 英文别名: (E)-1-(3,4-dihydropyrazol-2-yl)but-2-en-1-one
• CAS: 900188-86-5
• 化学式: C₇H₁₀N₂O
• 分子量: 138.169
• InChiKey: FAJLPDABJXDZKM-DUXPYHPUSA-N

物化性质

• 沸点：
  214.6±23.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4,5-dihydropyrazol-1-yl)but-2-en-1-one 在 盐酸 、 吡啶硼烷 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以31%的产率得到1-(pyrazolidin-1-yl)but-2-en-1-one
  参考文献：
  名称：

  Facile Scalable Reduction of N-Acylated Dihydropyrazoles

  摘要：

  The reduction of a variety of highly functionalized N-acylated dihydropyrazoles (1) with BH3, pyridine is described. The process through which this unexpectedly difficult reduction was discovered and developed is reported. A facile atom-efficient route to the N-acylated dihydropyrazole reduction precursors (1) is also illustrated. The resulting acylpyrazolidine products (2) that arise upon reduction were isolated in good to high yields following exposure to reaction conditions which have been shown to tolerate a variety of different functional groups. Finally, this route has been demonstrated on a kilogram scale and provides direct access to potential proline surrogates for peptidomimetic applications.

  DOI：

  10.1021/jo060567j
• 作为产物：
  描述：

  二氢吡唑 、 巴豆酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-(4,5-dihydropyrazol-1-yl)but-2-en-1-one
  参考文献：
  名称：

  Facile Scalable Reduction of N-Acylated Dihydropyrazoles

  摘要：

  The reduction of a variety of highly functionalized N-acylated dihydropyrazoles (1) with BH3, pyridine is described. The process through which this unexpectedly difficult reduction was discovered and developed is reported. A facile atom-efficient route to the N-acylated dihydropyrazole reduction precursors (1) is also illustrated. The resulting acylpyrazolidine products (2) that arise upon reduction were isolated in good to high yields following exposure to reaction conditions which have been shown to tolerate a variety of different functional groups. Finally, this route has been demonstrated on a kilogram scale and provides direct access to potential proline surrogates for peptidomimetic applications.

  DOI：

  10.1021/jo060567j

文献信息

• Facile Scalable Reduction of <i>N</i>-Acylated Dihydropyrazoles
  作者：Michael D. Curtis、Nancy C. Hayes、Patricia A. Matson

  DOI：10.1021/jo060567j

  日期：2006.6.1

  The reduction of a variety of highly functionalized N-acylated dihydropyrazoles (1) with BH3, pyridine is described. The process through which this unexpectedly difficult reduction was discovered and developed is reported. A facile atom-efficient route to the N-acylated dihydropyrazole reduction precursors (1) is also illustrated. The resulting acylpyrazolidine products (2) that arise upon reduction were isolated in good to high yields following exposure to reaction conditions which have been shown to tolerate a variety of different functional groups. Finally, this route has been demonstrated on a kilogram scale and provides direct access to potential proline surrogates for peptidomimetic applications.