(S)-2-amino-4,5,6-triphenyl-4H-pyran-3-carbonitrile | 1380076-98-1

• 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-4,5,6-triphenyl-4H-pyran-3-carbonitrile
• 英文别名: (4S)-2-amino-4,5,6-triphenyl-4H-pyran-3-carbonitrile
• CAS: 1380076-98-1
• 化学式: C₂₄H₁₈N₂O
• 分子量: 350.42
• InChiKey: JGLFCLXNUSNNSM-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 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：

  (E)-2-phenylchalcone 、 丙二腈 在 奎宁 作用下， 以 甲苯 为溶剂， 反应 60.0h， 以83%的产率得到
  参考文献：
  名称：

  Mechanistic Insights into Annulation of Arylidene‐Δ ² ‐Pyrrolin‐4‐Ones by Cinchona Squaramide‐Based Organocatalysts

  摘要：

  AbstractArylidene‐Δ2‐pyrrolin‐4‐ones undergo organocatalyzed annulation with malononitrile, furnishing dihydropyrano[3,2‐b]pyrroles (18 examples, 0–77% ee in dichloromethane, 11–44% ee in methanol). The products could be enantiomerically enriched by trituration (11 examples, 95–99% ee). Enantioselectivity was dependent on the nature of the substrate and the conformation of the catalyst, which in turn was solvent‐controlled. The reaction mechanism, which included two pseudo‐enantiomeric organocatalyst conformations, was investigated by experimental and quantum chemical methods. The reaction mechanism consists of Michael addition reaction step followed by 6‐exo‐dig annulation, which was found to be the rate determining step. Additionally, it was identified that the preferred reaction pathway follows the model originally proposed by Pápai et al.magnified image

  DOI：

  10.1002/adsc.202101369

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.
• Mechanistic Insights into Annulation of Arylidene‐Δ ² ‐Pyrrolin‐4‐Ones by Cinchona Squaramide‐Based Organocatalysts
  作者：Luka Ciber、Sebastijan Ričko、Jure Gregorc、Franc Požgan、Jurij Svete、Helena Brodnik、Bogdan Štefane、Uroš Grošelj

  DOI：10.1002/adsc.202101369

  日期：2022.3

  AbstractArylidene‐Δ2‐pyrrolin‐4‐ones undergo organocatalyzed annulation with malononitrile, furnishing dihydropyrano[3,2‐b]pyrroles (18 examples, 0–77% ee in dichloromethane, 11–44% ee in methanol). The products could be enantiomerically enriched by trituration (11 examples, 95–99% ee). Enantioselectivity was dependent on the nature of the substrate and the conformation of the catalyst, which in turn was solvent‐controlled. The reaction mechanism, which included two pseudo‐enantiomeric organocatalyst conformations, was investigated by experimental and quantum chemical methods. The reaction mechanism consists of Michael addition reaction step followed by 6‐exo‐dig annulation, which was found to be the rate determining step. Additionally, it was identified that the preferred reaction pathway follows the model originally proposed by Pápai et al.magnified image