1-benzyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline-3-carbonitrile
• 英文别名: 1-benzyl-2,5-dioxo-4,6,7,8-tetrahydro-3H-quinoline-3-carbonitrile
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: UTOKVVMLKMZWAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 N-benzyl-3-amino-2-cyclohexen-1-one 、 氰乙酸甲酯 在 lithium perchlorate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 14.0h， 以85%的产率得到1-benzyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  Lithium perchlorate-, acetic anhydride-, and triphenylphosphine-assisted multicomponent syntheses of 4-unsubstituted 2,5-dioxooctahydroquinoline-3-carboxylates and 3-carbonitriles

  摘要：

  Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates. When methyl cyanoacetate was subjected to the same reaction conditions in the presence of a catalytic amount of triphenylphosphine, the bicyclic 2,5-dioxooctahydroquinoline-3-carbonitriles were obtained in a one-flask reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.081

文献信息

• Lithium perchlorate-, acetic anhydride-, and triphenylphosphine-assisted multicomponent syntheses of 4-unsubstituted 2,5-dioxooctahydroquinoline-3-carboxylates and 3-carbonitriles
  作者：Xingxian Gu、Gunda I. Georg

  DOI：10.1016/j.tet.2013.08.081

  日期：2013.11

  Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates. When methyl cyanoacetate was subjected to the same reaction conditions in the presence of a catalytic amount of triphenylphosphine, the bicyclic 2,5-dioxooctahydroquinoline-3-carbonitriles were obtained in a one-flask reaction. (C) 2013 Elsevier Ltd. All rights reserved.