(E)-1,1'-(but-1-ene-1,3-diyl)bis(piperidin-2-one) | 1554189-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (E)-1,1'-(but-1-ene-1,3-diyl)bis(piperidin-2-one)
• 英文别名: 1-[(E)-3-(2-oxopiperidin-1-yl)but-1-enyl]piperidin-2-one
• CAS: 1554189-54-6
• 化学式: C₁₄H₂₂N₂O₂
• 分子量: 250.341
• InChiKey: ODEZTXSFBUVWHQ-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-乙烯基哌啶酮 在 gold(I) hexafluoroantimonate 、 苯乙炔 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以79%的产率得到(E)-1,1'-(but-1-ene-1,3-diyl)bis(piperidin-2-one)
  参考文献：
  名称：

  Head-to-tail homo- and heterodimerization of vinylamides by hidden proton catalysis

  摘要：

  Chemoselective dimerization of vinylamides is reported. A number of vinylacylamides were shown to undergo stereoselective cationic intermolecular head-to-tail homodimerization. Correspondingly, chemoselective heterodimerization reactions readily afforded hydroalkenylation of vinylacylamide with vinylsulfonamide. Different mild methods for hidden proton catalysis were studied. The in situ generation of, e.g., HSbF6 from the [Au]SbF6-PhC equivalent to CHI catalytic systems was applied. Successful vinylacylamide head-to-tail dimerizations seem to be dependant on the ability of N-C-O acylamide electron delocalization, affording stabilized intermediates. In general, the reactions demonstrate the ability of vinylacylamides to effectively undergo hydroalkenylation to afford 1,3-N,N-functionalized (E)-but-1-ene products. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.041

文献信息

• Head-to-tail homo- and heterodimerization of vinylamides by hidden proton catalysis
  作者：Naseem Iqbal、Guro Blakstad、Anne Fiksdahl

  DOI：10.1016/j.tet.2013.12.041

  日期：2014.2

  Chemoselective dimerization of vinylamides is reported. A number of vinylacylamides were shown to undergo stereoselective cationic intermolecular head-to-tail homodimerization. Correspondingly, chemoselective heterodimerization reactions readily afforded hydroalkenylation of vinylacylamide with vinylsulfonamide. Different mild methods for hidden proton catalysis were studied. The in situ generation of, e.g., HSbF6 from the [Au]SbF6-PhC equivalent to CHI catalytic systems was applied. Successful vinylacylamide head-to-tail dimerizations seem to be dependant on the ability of N-C-O acylamide electron delocalization, affording stabilized intermediates. In general, the reactions demonstrate the ability of vinylacylamides to effectively undergo hydroalkenylation to afford 1,3-N,N-functionalized (E)-but-1-ene products. (C) 2013 Elsevier Ltd. All rights reserved.