(R)-ethyl 6-amino-5-cyano-2,4-diphenyl-4H-pyran-3-carboxylate | 1380077-10-0

• 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: (R)-ethyl 6-amino-5-cyano-2,4-diphenyl-4H-pyran-3-carboxylate
• 英文别名: ethyl (4R)-6-amino-5-cyano-2,4-diphenyl-4H-pyran-3-carboxylate
• CAS: 1380077-10-0
• 化学式: C₂₁H₁₈N₂O₃
• 分子量: 346.386
• InChiKey: LJDWOPPGIKRIIK-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-benzoyl-3-phenylacrylate 、 丙二腈 在 奎宁 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (R)-ethyl 6-amino-5-cyano-2,4-diphenyl-4H-pyran-3-carboxylate 、 (S)-ethyl 6-amino-5-cyano-2,4-diphenyl-4H-pyran-3-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of 2-amino-4H-pyrans via the organocatalytic cascade reaction of malononitrile and α-substituted chalcones

  摘要：

  An organocatalytic cascade reaction of malononitrile and a-substituted chalcones has been developed for the synthesis of chiral multisubstituted 2-amino-4H-pyran derivatives. A series of chiral primary/tertiary amines and cinchona alkaloids were examined as the catalysts. Quinine was found to be the most efficient catalyst in the absence of any additive. The alpha-substitutents of the chalcones had a siginificant effect on the yield and the enantioselectivity. A number of multisubstituted 2-amino-4H-pyrans were obtained in excellent yields and enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.018

文献信息

• Enantioselective synthesis of 2-amino-4H-pyrans via the organocatalytic cascade reaction of malononitrile and α-substituted chalcones
  作者：Zhi-Peng Hu、Wei-Juan Wang、Xiao-Gang Yin、Xue-Jing Zhang、Ming Yan

  DOI：10.1016/j.tetasy.2012.03.018

  日期：2012.4

  An organocatalytic cascade reaction of malononitrile and a-substituted chalcones has been developed for the synthesis of chiral multisubstituted 2-amino-4H-pyran derivatives. A series of chiral primary/tertiary amines and cinchona alkaloids were examined as the catalysts. Quinine was found to be the most efficient catalyst in the absence of any additive. The alpha-substitutents of the chalcones had a siginificant effect on the yield and the enantioselectivity. A number of multisubstituted 2-amino-4H-pyrans were obtained in excellent yields and enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.