methyl 4-hydroxy-5-oxo-1,2-diphenyl-4-(trifluoromethyl)-4,5-dihydro-1H-pyrrole-3-carboxylate | 1616562-90-3

• 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: methyl 4-hydroxy-5-oxo-1,2-diphenyl-4-(trifluoromethyl)-4,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: 1,2-Diphenyl-4-hydroxy-4-(trifluoromethyl)-5-oxo-2-pyrroline-3-carboxylic acid methyl ester；methyl 4-hydroxy-5-oxo-1,2-diphenyl-4-(trifluoromethyl)pyrrole-3-carboxylate
• CAS: 1616562-90-3
• 化学式: C₁₉H₁₄F₃NO₄
• 分子量: 377.32
• InChiKey: CDRKMMZBQFPZNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,3,3-三氟丙酮酸乙酯 、 methyl (Z)-3-phenyl-3-(phenylamino)acrylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以95%的产率得到methyl 4-hydroxy-5-oxo-1,2-diphenyl-4-(trifluoromethyl)-4,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones with Brønsted acid-catalyzed condensation–cyclization reactions of β-enamino esters and ethyl trifluoropyruvate

  摘要：

  A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones based on trifluoroacetic acid-catalyzed condensation-cyclization reactions of beta-enamino esters and ethyl trifluoropyruvate is described. These reactions afford a series of alpha-trifluoromethylated gamma-lactam compounds in good to excellent yields under mild conditions. A preliminary trial of an asymmetric catalytic version with chiral BINOL-derived phosphoric acid as enantioselective catalyst was conducted and showed promising enantioselectivity of the desired product. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.052

文献信息

• A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones with Brønsted acid-catalyzed condensation–cyclization reactions of β-enamino esters and ethyl trifluoropyruvate
  作者：Qing-Lan Pei、Bao-Dong Cui、Wen-Yong Han、Zhi-Jun Wu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2014.05.052

  日期：2014.8

  A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones based on trifluoroacetic acid-catalyzed condensation-cyclization reactions of beta-enamino esters and ethyl trifluoropyruvate is described. These reactions afford a series of alpha-trifluoromethylated gamma-lactam compounds in good to excellent yields under mild conditions. A preliminary trial of an asymmetric catalytic version with chiral BINOL-derived phosphoric acid as enantioselective catalyst was conducted and showed promising enantioselectivity of the desired product. (C) 2014 Elsevier Ltd. All rights reserved.