[2-¹³C]-cyanoacetamide | 93664-98-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [2-¹³C]-cyanoacetamide
• 英文别名: [2-13C]-2-cyanoacetamide；2-cyanoacetamide
• CAS: 93664-98-3
• 化学式: C₃H₄N₂O
• 分子量: 85.0666
• InChiKey: DGJMPUGMZIKDRO-OUBTZVSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-二甲氧基丙酮 、 [2-¹³C]-cyanoacetamide 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 以71%的产率得到[2-13C]-2-cyano-4,4-dimethoxy-3-methylbut-2-enamide
  参考文献：
  名称：

  [2-13C]-和[3-13C]-3-Cyano-4-methyl-3-pyrrolin-2-one的高效制备

  摘要：

  [2-13C]-和[3-13C]-3-cyano-4-methyl-3-pyrrolin-2-one是通过新的合成路线制备的。α,α-二甲氧基酮在扩展的 Knoevenagel 反应中与双功能分子反应。该反应的产物通过几个步骤以高产率转化为具有生物学意义的 3-pyrrolin-2-ones。这种新方法还允许在环系统的许多位点进行简单的稳定同位素掺入。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600830
• 作为产物：
  描述：

  [2-¹³C]-cyanoacetic acid 在 草酰氯 、 氨 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 1.0h， 以74%的产率得到[2-¹³C]-cyanoacetamide
  参考文献：
  名称：

  [2-13C]-和[3-13C]-3-Cyano-4-methyl-3-pyrrolin-2-one的高效制备

  摘要：

  [2-13C]-和[3-13C]-3-cyano-4-methyl-3-pyrrolin-2-one是通过新的合成路线制备的。α,α-二甲氧基酮在扩展的 Knoevenagel 反应中与双功能分子反应。该反应的产物通过几个步骤以高产率转化为具有生物学意义的 3-pyrrolin-2-ones。这种新方法还允许在环系统的许多位点进行简单的稳定同位素掺入。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600830

文献信息

• Regiochemistry of the Condensation of 2-Aroyl-cyclohexanones and 2-Cyanoacetamide: ¹³C-Labeling Studies and Semiempirical MO Calculations
  作者：Oscar P. J. van Linden、Maikel Wijtmans、Luc Roumen、Lonneke Rotteveel、Rob Leurs、Iwan. J. P. de Esch

  DOI：10.1021/jo301138w

  日期：2012.9.7

  Hydroxy-aryl-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles represent interesting chemical scaffolds, but synthetic access to these compounds is limited. The reaction of 2-aroyl-cyclohexanones with 2-cyanoacetamide and base in ethanol has been reported to lead to the formation of the tetrahydroisoquinoline isomer. We show that depending on the electronic nature of the para-substituent on the aryl ring, formation of the regioisomeric tetrahydroquinoline isomer can significantly compete. The electron-donating or -withdrawing properties of the para-substituent of the aryl ring determines the ratio of product isomers. A series of 2-aroyl-cyclohexanones, with para-substituents ranging from electron-donating to electron-withdrawing, were reacted with [2-C-13]-cyanoacetamide. The product ratio and absolute regiochemistry were directly determined by quantitative C-13, HMBC, and NOESY NMR spectroscopy on the reaction mixtures. A clear relationship between the regioisomeric product ratio and the Hammett sigma values of the substituents is demonstrated. This is explained by the separate in situ yields, which reveal that the pathway leading to the tetrahydroquinoline regioisomer is significantly more sensitive toward the electronic nature of the para-substituent than the pathway leading to the tetrahydroisoquinoline. Semiempirical AM1 molecular orbital calculations on the starting electrophile 2-aroyl-cyclohexanone support a correlation between the energy of the LUMOs and the regioisomeric product ratio. Our results facilitate synthetic access to a range of these interesting synthetic intermediates.
• Efficient Preparation of [2-13C]- and [3-13C]-3-Cyano-4-methyl-3-pyrrolin-2-one
  作者：Prativa Bade Shrestha-Dawadi、Johan Lugtenburg

  DOI：10.1002/ejoc.200600830

  日期：2007.3

  [2-13C]- and [3-13C]-3-cyano-4-methyl-3-pyrrolin-2-one have been prepared by a new synthetic route. α,α-Dimethoxy ketones react with bifunctional molecules in an extended Knoevenagel reaction. The products of this reaction are converted in a few steps and in high yields into the biologically important 3-pyrrolin-2-ones. This new approach also allows simple stable isotope incorporation at many sites

  [2-13C]-和[3-13C]-3-cyano-4-methyl-3-pyrrolin-2-one是通过新的合成路线制备的。α,α-二甲氧基酮在扩展的 Knoevenagel 反应中与双功能分子反应。该反应的产物通过几个步骤以高产率转化为具有生物学意义的 3-pyrrolin-2-ones。这种新方法还允许在环系统的许多位点进行简单的稳定同位素掺入。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)