ethyl 1-benzyl-2-(naphthalen-2-yl)-4,5-dioxo-4,5-dihydro-1H-pyrrole-3-carboxylate | 1353748-20-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 1-benzyl-2-(naphthalen-2-yl)-4,5-dioxo-4,5-dihydro-1H-pyrrole-3-carboxylate
• CAS: 1353748-20-5
• 化学式: C₂₄H₁₉NO₄
• 分子量: 385.419
• InChiKey: IGYNQCBIJGOECW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzyl-2-(naphthalen-2-yl)-4,5-dioxo-4,5-dihydro-1H-pyrrole-3-carboxylate 、 丙酮 在 水 、 O-benzoyl-trans-4-hydroxy-L-proline 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以90%的产率得到ethyl (+)-1-benzyl-4-hydroxy-2-naphthalen-2-yl-5-oxo-4-(2-oxo-propyl)-4,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Organocatalyzed enantioselective aldol reaction of 1H-pyrrole-2,3-diones

  摘要：

  The enantioselective cross aldol reaction of 1-benzyl 4,5-dioxo-2-aryl-4,5-dihydro-1H-pyrrole-3-carboxylates and ketones was studied with praline derivatives or cinchona alkaloid-derived primary amines as the catalysts for the first time. trans-4-Benzoyloxy-L-proline (15) was found to be the best catalyst for acyclic ketones. For cyclohexanone, the best results were achieved with 9-deoxy-9-epi-aminoquinine (18) as the catalyst in the presence of racemic 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (19) as the cocatalyst. Using these protocols, 3-alkyl-3-hydroxy-1H-pyrrol-2(3H)-one derivatives were obtained in excellent yields and good to high ee values (up to 94% ee). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.056