(S)-2-amino-4,6-diphenyl-4H-pyran-3,5-dicarbonitrile | 1380077-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (S)-2-amino-4,6-diphenyl-4H-pyran-3,5-dicarbonitrile
• 英文别名: (4S)-2-amino-4,6-diphenyl-4H-pyran-3,5-dicarbonitrile
• CAS: 1380077-11-1
• 化学式: C₁₉H₁₃N₃O
• 分子量: 299.332
• InChiKey: YJIZQPMLTKLBLN-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-benzoyl-3-phenylacrylonitrile 、 丙二腈 在 奎宁 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (S)-2-amino-4,6-diphenyl-4H-pyran-3,5-dicarbonitrile 、 (R)-2-amino-4,6-diphenyl-4H-pyran-3,5-dicarbonitrile
  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

• Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans
  作者：Noha M. Hilmy Elnagdi、Noura Saad Al-Hokbany

  DOI：10.3390/molecules17044300

  日期：——

  The multicomponent reaction (MCR) of aromatic aldehydes 1 and malononitrile (2) with active methylenes 5a–h in the presence of L-proline produced pyrans and thiopyrans 6a–h stereospecifically and in good yields. Moreover a novel MCR of ethyl propiolate (8) with 1 and 2 in the presence of L-proline to afford (R)-polysubstituted pyran is also reported. X-ray structures, e.e. and optical activity of the synthesized compounds indicated that L-proline as a catalyst is responsible for the observed enantioselectivity in the studied reactions.

  在有 L-脯氨酸存在的情况下，芳香醛 1 和丙二腈 (2) 与活性亚甲基 5a-h 发生多组分反应 (MCR)，以良好的产率立体定向地生成了吡喃和硫代吡喃 6a-h。此外，还报道了在 L-脯氨酸存在下，丙炔酸乙酯（8）与 1 和 2 的新型 MCR 反应，生成 (R)-多取代吡喃。合成化合物的 X 射线结构、电子显微镜和光学活性表明，L-脯氨酸作为催化剂是所研究反应中观察到的对映体选择性的原因。