butyl 2-phenyl-1-methyl-4-(trifluoromethyl)pyrrole-3-carboxylate | 135106-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: butyl 2-phenyl-1-methyl-4-(trifluoromethyl)pyrrole-3-carboxylate
• 英文别名: Butyl 1-methyl-2-phenyl-4-(trifluoromethyl)pyrrole-3-carboxylate
• CAS: 135106-10-4
• 化学式: C₁₇H₁₈F₃NO₂
• 分子量: 325.331
• InChiKey: OCRNDOSNNHTMSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-Phenyl-3-methyl-5-oxazolonium- 、 butyl β-chloro-γ,γ,γ-trifluorocrotonate 在 三乙胺 作用下， 以 乙腈 为溶剂， 以33%的产率得到butyl 2-phenyl-1-methyl-4-(trifluoromethyl)pyrrole-3-carboxylate
  参考文献：
  名称：

  Synthesis of .beta.-(trifluoromethyl)pyrroles via the cycloaddition of munchnones to electron-deficient trifluoromethylated olefins

  摘要：

  The 1,3-dipolar cycloaddition of munchnones (1,3-oxazolium 5-olates) to beta-chloro-beta-(trifluoromethyl)vinyl phenyl ketone (1) and butyl beta-chloro-gamma,gamma,gamma-trifluorocrotonate (2) gave (trifluoromethyl)pyrroles. The monocyclic munchnones 3a-c yielded the beta-(trifluoromethyl)pyrroles 7a-c and 8a-c regiospecifically. The bicyclic and tricyclic munchnones 9a,b and 16a,b reacted with 1 and 2 to give mixtures of regioisomeric fused-ring trifluoromethylated pyrroles. In all instances, the unsaturated phenone 1 was more reactive than the crotonate 2. The cycloaddition of munchnones to the former occurred with a higher degree of regioselectivity.

  DOI：

  10.1021/jo00018a011