N-(2-iodoethene)-2-piperidinone | 1040743-32-5

• 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: N-(2-iodoethene)-2-piperidinone
• 英文别名: (E)-1-(2-iodovinyl)piperidin-2-one；1-[(E)-2-iodoethenyl]piperidin-2-one
• CAS: 1040743-32-5
• 化学式: C₇H₁₀INO
• 分子量: 251.067
• InChiKey: RDZQNKZRDHQDJT-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-iodoethene)-2-piperidinone 、 4-乙炔基苯甲醚 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以92%的产率得到(E)-1-(4-(4-methoxyphenyl)but-1-en-3-ynyl)piperidin-2-one
  参考文献：
  名称：

  Regioselective synthesis of β-iodo-enamides and β-yn-enamides

  摘要：

  Iodo-enamides were synthesised in a single step, in good yield and with complete selectivity from N-formyl imides. The beta-iodo-enamides are stable and were converted efficiently into novel geometrically defined beta-yn-enamides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.033
• 作为产物：
  描述：

  哌啶酮 在 chromium(III) chloride hexahydrate 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2-iodoethene)-2-piperidinone
  参考文献：
  名称：

  Regioselective synthesis of β-iodo-enamides and β-yn-enamides

  摘要：

  Iodo-enamides were synthesised in a single step, in good yield and with complete selectivity from N-formyl imides. The beta-iodo-enamides are stable and were converted efficiently into novel geometrically defined beta-yn-enamides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.033

文献信息

• Copper-promoted iodovinylation of amides: synthesis of β-functionalized enamides
  作者：Gabriel F. Sanapo、Benoit Daoust

  DOI：10.1016/j.tetlet.2008.03.157

  日期：2008.6

  We studied the addition of nitrogen radicals to ynol ethers in order to form beta-functionalized enamides. Poor yields are reported. On the other hand, we observed that copper coupling between 1,2-diiodoethene and various amides leads to beta-functionalized enamides in high yields with complete stereocontrol. (C) 2008 Elsevier Ltd. All rights reserved.
• Protecting Group Free, Stereocontrolled Synthesis of β-Halo-enamides
  作者：Adele E. Pasqua、James J. Crawford、De-Liang Long、Rodolfo Marquez

  DOI：10.1021/jo202130e

  日期：2012.3.2

  Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of beta-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol.