5-(1,1-difluoroethyl)-3-(2-furyl)-1-methyl-4,5-dihydro-1H-pyrazol-5-ol | 1024599-25-4

• 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: 5-(1,1-difluoroethyl)-3-(2-furyl)-1-methyl-4,5-dihydro-1H-pyrazol-5-ol
• 英文别名: 3-(1,1-difluoroethyl)-5-(furan-2-yl)-2-methyl-4H-pyrazol-3-ol
• CAS: 1024599-25-4
• 化学式: C₁₀H₁₂F₂N₂O₂
• 分子量: 230.214
• InChiKey: BSGGYMAINMBNAW-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  308.5±52.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(1,1-difluoroethyl)-3-(2-furyl)-1-methyl-4,5-dihydro-1H-pyrazol-5-ol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以98%的产率得到5-(1,1-difluoroethyl)-3-(2-furyl)-1-methylpyrazole
  参考文献：
  名称：

  通过使用氟化的醇作为溶剂提高吡唑形成中的区域选择性：氟化的Tebufenpyrad类似物的合成和生物活性

  摘要：

  The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.

  DOI：

  10.1021/jo800251g
• 作为产物：
  描述：

  4,4-二氟-1-(2-呋喃基)-1,3-戊二酮 、 甲基肼 以 乙醇 为溶剂， 反应 0.75h， 以54%的产率得到5-(1,1-difluoroethyl)-3-(2-furyl)-1-methyl-4,5-dihydro-1H-pyrazol-5-ol
  参考文献：
  名称：

  通过使用氟化的醇作为溶剂提高吡唑形成中的区域选择性：氟化的Tebufenpyrad类似物的合成和生物活性

  摘要：

  The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.

  DOI：

  10.1021/jo800251g

文献信息

• Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
  作者：Santos Fustero、Raquel Román、Juan F. Sanz-Cervera、Antonio Simón-Fuentes、Ana C. Cuñat、Salvador Villanova、Marcelo Murguía

  DOI：10.1021/jo800251g

  日期：2008.5.1

  The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.