4,4,5,5,5-五氟-1-(2-呋喃基)-1,3-戊二酮 | 2317-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4,4,5,5,5-五氟-1-(2-呋喃基)-1,3-戊二酮
• 英文名称: 4,4,5,5,5-pentafluoro-1-(2-furyl)-1,3-pentanedione
• 英文别名: 4,4,5,5,5-pentafluoro-1-furan-2-yl-pentane-1,3-dione；4,4,5,5,5-Pentafluor-1--pentan-1,3-dion；4,4,5,5,5-Pentafluoro-1-(2-furyl)pentane-1,3-dione；4,4,5,5,5-pentafluoro-1-(furan-2-yl)pentane-1,3-dione
• CAS: 2317-66-0
• 化学式: C₉H₅F₅O₃
• 分子量: 256.129
• InChiKey: FBFKOUOYDDHGMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  232.5±35.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,4,5,5,5-五氟-1-(2-呋喃基)-1,3-戊二酮 、 苯肼 以 various solvent(s) 为溶剂， 反应 0.75h， 以93%的产率得到3-(1,1,2,2,2-pentafluoroethyl)-5-(2-furyl)-1-phenylpyrazole
  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：

  2-乙酰基呋喃 、 五氟丙酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.5h， 以73%的产率得到4,4,5,5,5-五氟-1-(2-呋喃基)-1,3-戊二酮
  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

• Synthesis of Fluorinated and Nonfluorinated Tebufenpyrad Analogues for the Study of Anti-angiogenesis MOA
  作者：Raquel Román、Antonio Navarro、Dariusz Wodka、Maria Alvim-Gaston、Saba Husain、Natalie Franklin、Antonio Simón-Fuentes、Santos Fustero

  DOI：10.1021/op500114v

  日期：2014.8.15
• 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.