N-(2-iodoethene)-2-pyrrolidinone | 1040743-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(2-iodoethene)-2-pyrrolidinone
• 英文别名: (E)-1-(2-iodovinyl)pyrrolidin-2-one；1-(2-Iodoethenyl)pyrrolidine-2-one；1-[(E)-2-iodoethenyl]pyrrolidin-2-one
• CAS: 1040743-30-3
• 化学式: C₆H₈INO
• 分子量: 237.04
• InChiKey: RDZHARZRINKLMR-HWKANZROSA-N

物化性质

• 熔点：
  28 °C
• 沸点：
  286.4±19.0 °C(Predicted)
• 密度：
  2.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 在 N-碘代丁二酰亚胺 、 氯化(双三环己基膦)(一氧化碳)(氢)钌 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 26.0h， 生成 N-(2-iodoethene)-2-pyrrolidinone
  参考文献：
  名称：

  N-乙烯基酰胺的硅辅助合成（E）-β-卤代烯酰胺

  摘要：

  （E）-β-碘烯酰胺和（E）-β-碘烯酰亚胺可以很容易地从N-乙烯基衍生物（N-乙烯基酰胺和N-乙烯基酰亚胺）中通过立体选择性钌催化的硅烷化与乙烯基三甲基硅烷偶联（Marciniec偶联）而获得–碘交换。（E）-β-硅酰亚胺的溴代甲硅烷基化可提供（E）-β-溴亚胺，而涉及（E）-β-硅酰胺的类似反应会导致底物分解。ñ‐卤代琥珀酰亚胺在温和条件下的去甲硅烷基化步骤中被发现是最有效的卤化剂。钌催化的甲硅烷基化/卤代甲硅烷基化序列可以一锅法进行。版权所有©2015 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/aoc.3284

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.
• Regioselective synthesis of β-iodo-enamides and β-yn-enamides
  作者：Adele E. Pasqua、Lynne H. Thomas、James J. Crawford、Rodolfo Marquez

  DOI：10.1016/j.tet.2011.07.033

  日期：2011.9

  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.