2-cyano-3-(3-fluorophenyl)acrylamide | 100908-62-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-cyano-3-(3-fluorophenyl)acrylamide
• 英文别名: 2-Cyano-3-(m-fluorophenyl)acrylamide；2-cyano-3-(3-fluorophenyl)prop-2-enamide
• CAS: 100908-62-1
• 化学式: C₁₀H₇FN₂O
• 分子量: 190.177
• InChiKey: NVGNGLIOIXXMRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  1-(2-methoxy-2-oxoethyl)pyridin-1-ium bromide 、 2-cyano-3-(3-fluorophenyl)acrylamide 在 三乙胺 作用下， 以 乙醇 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  Stereoselective Synthesis oftrans-4,5-Substituted 1,4,5,6-tetrahydropyridine-2-(olates)thiolates

  摘要：

  反式-4,5-取代的 1,4,5,6-四氢吡啶-2-（橄榄酸盐）硫醇酯可由吡啶鎓盐和氰乙酸衍生物制备，或由吡啶鎓盐、芳香醛和氰乙酸乙酯或氰乙酰胺在碱存在下制备。

  DOI：

  10.1055/s-1991-26477
• 作为产物：
  描述：

  氰乙酰胺 、 3-氟苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-cyano-3-(3-fluorophenyl)acrylamide
  参考文献：
  名称：

  Tuning the Electronic Properties of 2-Cyano-3-phenylacrylamide Derivatives

  摘要：

  We are the first to report the synthesis of a new class of 2-cyanoarylacrylamide (2-CAA) derivatives and observe that the synthesized 2-CAA shows fluorescence properties due to the formation of a dimeric interaction of hydrogen bonds between carbonyl oxygens and amide hydrogens (C=O center dot center dot center dot H-N-C=O center dot center dot center dot H-N center dot center dot center dot); i.e., dimers are linked through dimeric N-H center dot center dot center dot O hydrogen bonds. The single-crystal X-ray structure shows molecules to be hydrogen-bonded dimers, which further form a parallel stacking arrangement, mediated by significant pi-pi interactions. The H-1 NMR and fluorescence spectral studies indicate the coexistence of amide and iminol tautomers in solution, which can be influenced by the nature of the solvent. Further, the excitation-wavelength-dependent fluorescence spectrum and the biexponential fluorescence decay profiles suggest the presence of more than one emitting species; i.e., amide and iminol tautomers coexists in solution. We have also shown that the equilibrium between the two tautomers can be tuned by the judicious choice of electron-donating or -withdrawing substituents.

  DOI：

  10.1021/acs.joc.5b02226

文献信息

• Tuning the Electronic Properties of 2-Cyano-3-phenylacrylamide Derivatives
  作者：Ramachandran Gunasekar、Pichandi Thamaraiselvi、Ravindranath S. Rathore、Kulathu Iyer Sathiyanarayanan、Shanmugam Easwaramoorthi

  DOI：10.1021/acs.joc.5b02226

  日期：2015.12.18

  We are the first to report the synthesis of a new class of 2-cyanoarylacrylamide (2-CAA) derivatives and observe that the synthesized 2-CAA shows fluorescence properties due to the formation of a dimeric interaction of hydrogen bonds between carbonyl oxygens and amide hydrogens (C=O center dot center dot center dot H-N-C=O center dot center dot center dot H-N center dot center dot center dot); i.e., dimers are linked through dimeric N-H center dot center dot center dot O hydrogen bonds. The single-crystal X-ray structure shows molecules to be hydrogen-bonded dimers, which further form a parallel stacking arrangement, mediated by significant pi-pi interactions. The H-1 NMR and fluorescence spectral studies indicate the coexistence of amide and iminol tautomers in solution, which can be influenced by the nature of the solvent. Further, the excitation-wavelength-dependent fluorescence spectrum and the biexponential fluorescence decay profiles suggest the presence of more than one emitting species; i.e., amide and iminol tautomers coexists in solution. We have also shown that the equilibrium between the two tautomers can be tuned by the judicious choice of electron-donating or -withdrawing substituents.
• Stereoselective Synthesis of<i>trans</i>-4,5-Substituted 1,4,5,6-tetrahydropyridine-2-(olates)thiolates
  作者：A. M. Shestopalov、V. P. Litvinov、L. A. Rodinovskaya、Yu. A. Sharanin

  DOI：10.1055/s-1991-26477

  日期：——

  trans-4,5-Substituted 1,4,5,6-tetrahydropyridine-2-(olates)thiolates are prepared either from pyridinium salts and cyanoacetic acid derivatives or from pyridinium salts, aromatic aldehydes and ethyl cyanoacetate or cyanoacetamide in the presence of a base.

  反式-4,5-取代的 1,4,5,6-四氢吡啶-2-（橄榄酸盐）硫醇酯可由吡啶鎓盐和氰乙酸衍生物制备，或由吡啶鎓盐、芳香醛和氰乙酸乙酯或氰乙酰胺在碱存在下制备。