(S,S)-4-oxo-2,6-bis(4-methylphenyl)-1,1-cyclohexanedicarbonitrile | 1262238-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,S)-4-oxo-2,6-bis(4-methylphenyl)-1,1-cyclohexanedicarbonitrile
• 英文别名: (2S,6S)-4-oxo-2,6-di-p-tolylcyclohexane-1,1-dicarbonitrile；(2S,6S)-2,6-bis(4-methylphenyl)-4-oxocyclohexane-1,1-dicarbonitrile
• CAS: 1262238-62-9
• 化学式: C₂₂H₂₀N₂O
• 分子量: 328.414
• InChiKey: WFGZOUAEKXVBPC-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  bis(4-methylstyryl)ketone 、 丙二腈 在 奎宁胺 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以75%的产率得到(S,S)-4-oxo-2,6-bis(4-methylphenyl)-1,1-cyclohexanedicarbonitrile
  参考文献：
  名称：

  Asymmetric Organocatalytic Double-Conjugate Addition of Malononitrile to Dienones: Efficient Synthesis of Optically Active Cyclohexanones

  摘要：

  9-Amino-9-deoxyepiquinine efficiently catalyzed the double-conjugate addition of malononitrile to dienones. A number of 1,1,2,6-tetrasubstituted cyclohexanones were prepared in good yields, diastereoselectivities, and excellent enantioselectivities.

  DOI：

  10.1021/ol102570b

文献信息

• Quinine-Catalysed Double Michael Addition of Malononitrile to 1,5-Disubstituted Pentadien-3-ones: A Stereoselective Route to Cyclohexanones
  作者：Claudia De Fusco、Alessandra Lattanzi

  DOI：10.1002/ejoc.201100282

  日期：2011.7

  The stereoselective synthesis of 4-oxo-2,6-diaryl-cyclohexane-1,1-dicarbonitriles has been developed through double Michael addition of malononitrile to 1,5-disubstituted pentadien-3-ones catalysed by quinine. This simple cascade process affords cyclohexanones in moderate-to-good yields, excellent diastereoselectivity and up to 86 % ee. The isolation of the monoaddition product helps to shed light

  4-氧代-2,6-二芳基-环己烷-1,1-二腈的立体选择性合成是通过丙二腈与奎宁催化的1,5-二取代戊二烯-3-酮的双迈克尔加成而开发的。这种简单的级联过程以中等至良好的产率、出色的非对映选择性和高达 86% 的 ee 提供了环己酮。单加成产物的分离有助于阐明两步法的立体化学结果。
• Asymmetric Organocatalytic Double-Conjugate Addition of Malononitrile to Dienones: Efficient Synthesis of Optically Active Cyclohexanones
  作者：Xue-ming Li、Bo Wang、Jun-min Zhang、Ming Yan

  DOI：10.1021/ol102570b

  日期：2011.2.4

  9-Amino-9-deoxyepiquinine efficiently catalyzed the double-conjugate addition of malononitrile to dienones. A number of 1,1,2,6-tetrasubstituted cyclohexanones were prepared in good yields, diastereoselectivities, and excellent enantioselectivities.