ethyl 1-benzyl-4-hydroxy-5-oxo-4-(2-oxocyclohexyl)-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylate | 1353748-11-4

• 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-4-hydroxy-5-oxo-4-(2-oxocyclohexyl)-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: Ethyl 1-benzyl-4-hydroxy-5-oxo-4-(2-oxocyclohexyl)-2-phenylpyrrole-3-carboxylate；ethyl 1-benzyl-4-hydroxy-5-oxo-4-(2-oxocyclohexyl)-2-phenylpyrrole-3-carboxylate
• CAS: 1353748-11-4
• 化学式: C₂₆H₂₇NO₅
• 分子量: 433.504
• InChiKey: IPFIKMCFLODKID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环己酮 、 4-ethoxycarbonyl-5-phenyl-N-benzyldioxopyrroline 在 奎宁胺 、 S-联萘酚磷酸酯 作用下， 反应 96.0h， 以94%的产率得到ethyl 1-benzyl-4-hydroxy-5-oxo-4-(2-oxocyclohexyl)-2-phenyl-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

文献信息

• Organocatalyzed enantioselective aldol reaction of 1H-pyrrole-2,3-diones
  作者：Mayur Bhanushali、Cong-Gui Zhao

  DOI：10.1016/j.tetlet.2011.11.056

  日期：2012.1

  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.