methyl 3-hydroxy-1-phenyl-5-(4-(trifluoromethyl)phenyl)-1H-pyrrole-2-carboxylate | 1344025-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 3-hydroxy-1-phenyl-5-(4-(trifluoromethyl)phenyl)-1H-pyrrole-2-carboxylate
• 英文别名: Methyl 3-hydroxy-1-phenyl-5-[4-(trifluoromethyl)phenyl]pyrrole-2-carboxylate；methyl 3-hydroxy-1-phenyl-5-[4-(trifluoromethyl)phenyl]pyrrole-2-carboxylate
• CAS: 1344025-78-0
• 化学式: C₁₉H₁₄F₃NO₃
• 分子量: 361.32
• InChiKey: XZQPDVJOQOFIGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-phenyl-1-(4-(trifluoromethyl)phenyl)methanimine oxide 在 盐酸 、 rhodium(II) acetate dimer 、 copper(I) hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 methyl 3-hydroxy-1-phenyl-5-(4-(trifluoromethyl)phenyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Multifunctionalized 3-Hydroxypyrroles in a Three-Step, One-Pot Cascade Process from Methyl 3-TBSO-2-diazo-3-butenoate and Nitrones

  摘要：

  The synthesis of N-aryl-2-carboxyl-3-hydroxy-5-arylpyrroles has been achieved in high yield by the combination of a TBSO-substituted vinyldiazoacetate and nitrones in a one-pot cascade process involving copper-catalyzed Mannich addition, dirhodium-catalyzed dinitrogen extrusion and N-OTBS insertion, and acid-promoted aromatization (elimination).

  DOI：

  10.1021/ol2026125

文献信息

• Multifunctionalized 3-Hydroxypyrroles in a Three-Step, One-Pot Cascade Process from Methyl 3-TBSO-2-diazo-3-butenoate and Nitrones
  作者：Xinfang Xu、Maxim O. Ratnikov、Peter Y. Zavalij、Michael P. Doyle

  DOI：10.1021/ol2026125

  日期：2011.11.18

  The synthesis of N-aryl-2-carboxyl-3-hydroxy-5-arylpyrroles has been achieved in high yield by the combination of a TBSO-substituted vinyldiazoacetate and nitrones in a one-pot cascade process involving copper-catalyzed Mannich addition, dirhodium-catalyzed dinitrogen extrusion and N-OTBS insertion, and acid-promoted aromatization (elimination).