3-(呋喃-2-基)-1-苯基-5-(三氟甲基)吡唑 | 193816-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(呋喃-2-基)-1-苯基-5-(三氟甲基)吡唑
• 英文名称: 3-(furan-2-yl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole
• 英文别名: 5-trifluoromethyl-3-(2-furyl)-1-phenyl-1H-pyrazole；1H-Pyrazole, 3-(2-furanyl)-1-phenyl-5-(trifluoromethyl)-；3-(furan-2-yl)-1-phenyl-5-(trifluoromethyl)pyrazole
• CAS: 193816-18-1
• 化学式: C₁₄H₉F₃N₂O
• 分子量: 278.233
• InChiKey: SATFCBFOGKJSDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴-3,3,3-三氟丙烯 、 N'-phenylfuran-2-carbohydrazonoyl chloride 在 三乙烯二胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 24.0h， 以78%的产率得到3-(呋喃-2-基)-1-苯基-5-(三氟甲基)吡唑
  参考文献：
  名称：

  [3 + 2]腈亚胺和2-溴-3,3,3-三氟丙烯的[3 + 2]环加成反应选择性合成5-三氟甲基吡唑

  摘要：

  据报道，通过将酰氯与环境友好的大吨位工业原料2-溴-3,3,3-三氟丙烯（BTP）偶合，可以合成5-三氟甲基吡唑的通用方法。腈亚胺和BTP的这种唯一的区域选择性[3 + 2]环加成反应无催化剂，操作简单，具有温和的条件，高收率，可克级缩放，广泛的底物范围和有价值的官能团耐受性。重要的是，我们的方法已用于合成鞘氨醇1-磷酸受体活性激动剂的关键中间体。

  DOI：

  10.1021/acs.joc.0c02765

文献信息

• Regioselective Synthesis of 5-Trifluoromethyl Pyrazoles by the [1+4] Cyclization of Phenylhydrazones with N-Aryl Trifluoroacetimidoyl Iodides
  作者：Hong-Bin Yu、Wei-Yuan Huang

  DOI：10.1055/s-1997-3274

  日期：1997.6

  Treatment of the phenylhydrazone of a methyl ketone (2) or cyclohexanone (3) with N-aryl trifluoroacetimidoyl iodide (1) in the presence of excess sodium hydride resulted in a [1+4] cyclization to give 5-trifluoromethyl pyrazoles (4, 5) regioselectively. The structure of products 4 or 5 was confirmed by the 13C NMR spectra.

  用过量氢化钠处理甲基酮（2）或环己酮（3）的苯肼酮与N-芳基三氟乙酰肟碘化物（1）反应，发生了[1+4]环化反应，选择性地产生5-三氟甲基吡唑（4, 5）。产品4或5的结构通过13C NMR谱得到了确认。
• Haloacetylated Enol Ethers, 19: Synthesis of 3-(2-Thienyl)- and 3-(2-Furyl)-5-trihalomethyl Substituted Azoles
  作者：Alex Flores、Sergio Brondani、Lucas Pizzuti、Marcos Martins、Nilo Zanatta、Helio Bonacorso、Darlene Flores

  DOI：10.1055/s-2005-872140

  日期：——

  Heterocyclization of 1,1,1-trifluoro[chloro]-4-methoxy-4-[2-tienyl]-3-buten-2-one and 1,1,1-trifluoro[chloro]-4-methoxy-4-[2-furyl]-3-buten-2-ones into isoxazoles and pyrazoles derivatives as a new type of trihalomethylated bicyclic heterocycles is reported.

  1,1,1-三氟[氯]-4-甲氧基-4-[2-噻吩基]-3-丁烯-2-酮和1,1,1-三氟[氯]-4-甲氧基-4-的杂环化报道了将[2-呋喃基]-3-丁烯-2-酮转化为异恶唑和吡唑衍生物作为新型三卤甲基化双环杂环。
• Insecticidal anthranilic diamides: A new class of potent ryanodine receptor activators
  作者：George P. Lahm、Thomas P. Selby、John H. Freudenberger、Thomas M. Stevenson、Brian J. Myers、Gilles Seburyamo、Ben K. Smith、Lindsey Flexner、Christopher E. Clark、Daniel Cordova

  DOI：10.1016/j.bmcl.2005.08.034

  日期：2005.11

  A novel class of anthranilic diamides has been discovered with exceptional insecticidal activity on a range of Lepidoptera. These compounds have been found to exhibit their action by release of intracellular Ca2+ stores mediated by the ryanodine receptor. The discovery, synthesis, structure-activity, and biological results are presented. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.
• New strategy for the regioselective synthesis of 1-phenyl-3-trifluoromethyl-1H-pyrazoles
  作者：Nilo Zanatta、Simone S. Amaral、Josiane M. dos Santos、Andréia M.P.W. da Silva、Juliana M.F.M. Schneider、Liana da S. Fernandes、Helio G. Bonacorso、Marcos A.P. Martins

  DOI：10.1016/j.tetlet.2013.05.103

  日期：2013.7

  A regioselective synthesis of 3-trifluoromethyl-1-phenyl-1H-pyrazoles (1,3-isomers) as well as their 1,5-isomers (5-trifluoromethyl-1-phenyl-1H-pyrazoles), is described. The 1,3-isomers were obtained from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones with arylhydrazones followed by deprotective hydrolysis while the 1,5-isomer was obtained by direct cyclocondensation of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones with phenylhydrazine. An unequivocal assignment of the 1,3- and 1,5-isomers of the pyrazole products is given. (C) 2013 Elsevier Ltd. All rights reserved.