4-trifluoromethyl-1-methyl-2-phenyl-1H-pyrrole | 1253394-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-trifluoromethyl-1-methyl-2-phenyl-1H-pyrrole
• 英文别名: 4-trifluoromethyl-1-methyl-2-phenylpyrrole；1-Methyl-4-(trifluoromethyl)-2-phenylpyrrole；1-methyl-2-phenyl-4-(trifluoromethyl)pyrrole
• CAS: 1253394-12-5
• 化学式: C₁₂H₁₀F₃N
• 分子量: 225.213
• InChiKey: ULDLAULBLOCFSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙醇 、 4-trifluoromethyl-1-methyl-2-phenyl-1H-pyrrole 在 三氟乙酸 作用下， 以80%的产率得到ethyl 1-methyl-5-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  New Synthesis of 3-Trifluoromethylpyrroles by Condensation of Mesoionic 4-Trifluoroacetyl-1,3-oxazolium-5-olates with Phosphorus Ylides

  摘要：

  Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines with trifluoroacetic anhydride, react with phosphorus ylides to give beta-trifluoromethylpyrroles (2) in good yields. The novel ring transformations of 1 into 2 occur via an initial attack of the ylide anions on the C-2 position of the ring.

  DOI：

  10.1021/ol1018689
• 作为产物：
  描述：

  三甲基硅基甲基三苯基碘化磷 、 4-trifluoroacetyl-3-methyl-2-phenyl-1,3-oxazolium-5-olate 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以47%的产率得到4-trifluoromethyl-1-methyl-2-phenyl-1H-pyrrole
  参考文献：
  名称：

  New Synthesis of 3-Trifluoromethylpyrroles by Condensation of Mesoionic 4-Trifluoroacetyl-1,3-oxazolium-5-olates with Phosphorus Ylides

  摘要：

  Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines with trifluoroacetic anhydride, react with phosphorus ylides to give beta-trifluoromethylpyrroles (2) in good yields. The novel ring transformations of 1 into 2 occur via an initial attack of the ylide anions on the C-2 position of the ring.

  DOI：

  10.1021/ol1018689

文献信息

• The use of sulfur ylides in the synthesis of 3-alkyl(aryl)thio-4-trifluoromethylpyrroles from mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates
  作者：Ryosuke Saijo、Masami Kawase

  DOI：10.1016/j.tetlet.2012.03.130

  日期：2012.5

  In this report, we describe a new method for the synthesis of densely functionalized pyrroles. Reaction of mesoionic 1,3-oxazolium-5-olates with various S-ylides proceeds via nucleophilic addition followed by opening of the oxazole ring and subsequent cyclization to multisubstituted pyrroles bearing both a trifluoromethyl and alkyl(aryl)thio group at 3- and 4-positions.

  在这份报告中，我们描述了一种合成高密度官能化吡咯的新方法。通过亲核加成反应，使中离子1,3-恶唑基5-油酸酯与各种S-基化物反应，然后打开恶唑环，随后环化成在3-和4位同时带有三氟甲基和烷基（芳基）硫基的多取代吡咯-位置。
• New Synthesis of 3-Trifluoromethylpyrroles by Condensation of Mesoionic 4-Trifluoroacetyl-1,3-oxazolium-5-olates with Phosphorus Ylides
  作者：Ryosuke Saijo、Yuri Hagimoto、Masami Kawase

  DOI：10.1021/ol1018689

  日期：2010.11.5

  Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines with trifluoroacetic anhydride, react with phosphorus ylides to give beta-trifluoromethylpyrroles (2) in good yields. The novel ring transformations of 1 into 2 occur via an initial attack of the ylide anions on the C-2 position of the ring.