(S)-2-amino-4-(4-chlorophenyl)-5,6-diphenyl-4H-pyran-3-carbonitrile | 1380076-99-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (S)-2-amino-4-(4-chlorophenyl)-5,6-diphenyl-4H-pyran-3-carbonitrile
• 英文别名: (4S)-2-amino-4-(4-chlorophenyl)-5,6-diphenyl-4H-pyran-3-carbonitrile
• CAS: 1380076-99-2
• 化学式: C₂₄H₁₇ClN₂O
• 分子量: 384.865
• InChiKey: LGDNAAREDMXZNN-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(4-chlorophenyl)-1,2-diphenyl-propenone 、 丙二腈 在 奎宁 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 (S)-2-amino-4-(4-chlorophenyl)-5,6-diphenyl-4H-pyran-3-carbonitrile 、 (R)-2-amino-4-(4-chlorophenyl)-5,6-diphenyl-4H-pyran-3-carbonitrile
  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.