2-Benzyl-4,4,4-trifluoro-3,3-dihydroxybutanenitrile | 504408-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Benzyl-4,4,4-trifluoro-3,3-dihydroxybutanenitrile
• 英文别名: 2-benzyl-4,4,4-trifluoro-3,3-dihydroxybutanenitrile
• CAS: 504408-38-2
• 化学式: C₁₁H₁₀F₃NO₂
• 分子量: 245.201
• InChiKey: HTNXMOZWIKOXDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Benzyl-4,4,4-trifluoro-3,3-dihydroxybutanenitrile 以 乙腈 为溶剂， 反应 4.0h， 生成 5-benzyl-2,4-diamino-6-(trifluoromethyl)pyrimidine
  参考文献：
  名称：

  Selective synthesis of fluorinated benzyl- or phenylpyrimidines from the heterocyclisation of α-trifluoroacetylarylpropanenitriles

  摘要：

  Some 5-benzyl-6-trifluoromethyl-2,4-diaminopyrimidines analogous to trimethoprim and 6-aryl -5-trifluoroethyl-2,4-diaminopyrimidines analogous to pyrimethamine were prepared from the same synthons, trifluoromethylated P-ketonitriles. The heterocyclisation between enol ether of beta-ketonitrile and guanidine leading to these compounds was studied. These fluorinated novel compounds were tested for their in vitro activity against Toxoplasma gondii, a widespread apicomplexan protozoa responsible for congenital toxoplasmosis and cerebral toxoplasmosis in immunocompromised patients. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.05.014
• 作为产物：
  描述：

  三氟乙酸乙酯 、 苯代丙腈 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以75%的产率得到2-Benzyl-4,4,4-trifluoro-3,3-dihydroxybutanenitrile
  参考文献：
  名称：

  Unexpected synthesis of (trifluoroethyl)pyrimidines from the heterocyclisation of α-trifluoroacetylpropanenitriles

  摘要：

  Some 4-trifluoromethyl-2-aminopyrimidines analogous to trimethoprim and 5-trifluoroethyl-2,4-diaminopyrimidines analogous to pyrimethamine were prepared from enamino(trifluoromethyl)ketones and alpha-trifluoroacetylpropanenitriles, respectively. A novel heterocyclisation between a trifluoromethylated beta-ketonitrile and guanidine was described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02245-1

文献信息

• Unexpected synthesis of (trifluoroethyl)pyrimidines from the heterocyclisation of α-trifluoroacetylpropanenitriles
  作者：Hatice Berber、Mustapha Soufyane、Maud Santillana-Hayat、Catherine Mirand

  DOI：10.1016/s0040-4039(02)02245-1

  日期：2002.12

  Some 4-trifluoromethyl-2-aminopyrimidines analogous to trimethoprim and 5-trifluoroethyl-2,4-diaminopyrimidines analogous to pyrimethamine were prepared from enamino(trifluoromethyl)ketones and alpha-trifluoroacetylpropanenitriles, respectively. A novel heterocyclisation between a trifluoromethylated beta-ketonitrile and guanidine was described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Selective synthesis of fluorinated benzyl- or phenylpyrimidines from the heterocyclisation of α-trifluoroacetylarylpropanenitriles
  作者：Hatice Berber、Catherine Mirand、Francis Derouin

  DOI：10.1016/j.jfluchem.2007.05.014

  日期：2007.9

  Some 5-benzyl-6-trifluoromethyl-2,4-diaminopyrimidines analogous to trimethoprim and 6-aryl -5-trifluoroethyl-2,4-diaminopyrimidines analogous to pyrimethamine were prepared from the same synthons, trifluoromethylated P-ketonitriles. The heterocyclisation between enol ether of beta-ketonitrile and guanidine leading to these compounds was studied. These fluorinated novel compounds were tested for their in vitro activity against Toxoplasma gondii, a widespread apicomplexan protozoa responsible for congenital toxoplasmosis and cerebral toxoplasmosis in immunocompromised patients. (c) 2007 Elsevier B.V. All rights reserved.