3-Ethyl-2,6-di-furan-2-yl-piperidin-4-one | 494791-66-1

• 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: 3-Ethyl-2,6-di-furan-2-yl-piperidin-4-one
• 英文别名: 3-ethyl-2,6-bis(furan-2-yl)piperidin-4-one
• CAS: 494791-66-1
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: RGNPXEMHSDVXIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Ethyl-2,6-di-furan-2-yl-piperidin-4-one 在 盐酸羟胺 、 sodium acetate 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 N-nitroso-3-ethyl-2,6-di-2-furylpiperidin-4-one oxime
  参考文献：
  名称：

  Synthesis, spectral, theoretical, and antimicrobial screening of some heterocyclic oximes

  摘要：

  In a wide research program toward new and efficient antimicrobial agents, a series of substituted N-nitroso-3-alkyl piperidone oximes were synthesized and their antibacterial activity against Staphylococcus aureus, Pseudomonas aerugonisa, Escherichia coli, and Klbesiella pneumoniae and antifungal activity against Aspergillus niger, Aspergillus flavus, and Rhizopus were evaluated. Their structure and stereochemistry were characterized by high-resolution H-1 NMR, mass and elemental analysis. The spectra of all N-nitroso oximes reveal the presence of two isomers labeled as E (-NOH group is anti to N-N=O moiety) and Z (-NOH group is syn to N-N=O moiety) in solution and the coupling constants ruled out the possibility of normal chair conformation. From the theoretical studies and coupling constant values, it was found that all N-nitroso oximes exist as an equilibrium mixture of CA boat conformation (B (1)) and the major isomer was found to be E isomer. The molecular structure of N-nitroso oximes were also determined by semiempirical and Gaussian-03 calculation and the results are in agreement with the experimental studies.

  DOI：

  10.1007/s00044-010-9427-x
• 作为产物：
  描述：

  糠醛 、 2-戊酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 生成 3-Ethyl-2,6-di-furan-2-yl-piperidin-4-one
  参考文献：
  名称：

  Synthesis, spectral, theoretical, and antimicrobial screening of some heterocyclic oximes

  摘要：

  In a wide research program toward new and efficient antimicrobial agents, a series of substituted N-nitroso-3-alkyl piperidone oximes were synthesized and their antibacterial activity against Staphylococcus aureus, Pseudomonas aerugonisa, Escherichia coli, and Klbesiella pneumoniae and antifungal activity against Aspergillus niger, Aspergillus flavus, and Rhizopus were evaluated. Their structure and stereochemistry were characterized by high-resolution H-1 NMR, mass and elemental analysis. The spectra of all N-nitroso oximes reveal the presence of two isomers labeled as E (-NOH group is anti to N-N=O moiety) and Z (-NOH group is syn to N-N=O moiety) in solution and the coupling constants ruled out the possibility of normal chair conformation. From the theoretical studies and coupling constant values, it was found that all N-nitroso oximes exist as an equilibrium mixture of CA boat conformation (B (1)) and the major isomer was found to be E isomer. The molecular structure of N-nitroso oximes were also determined by semiempirical and Gaussian-03 calculation and the results are in agreement with the experimental studies.

  DOI：

  10.1007/s00044-010-9427-x

文献信息

• Synthesis, spectral, theoretical, and antimicrobial screening of some heterocyclic oximes
  作者：Jayaraman Jayabharathi、Annamalai Manimekalai、Manoharan Padmavathy

  DOI：10.1007/s00044-010-9427-x

  日期：2011.9

  In a wide research program toward new and efficient antimicrobial agents, a series of substituted N-nitroso-3-alkyl piperidone oximes were synthesized and their antibacterial activity against Staphylococcus aureus, Pseudomonas aerugonisa, Escherichia coli, and Klbesiella pneumoniae and antifungal activity against Aspergillus niger, Aspergillus flavus, and Rhizopus were evaluated. Their structure and stereochemistry were characterized by high-resolution H-1 NMR, mass and elemental analysis. The spectra of all N-nitroso oximes reveal the presence of two isomers labeled as E (-NOH group is anti to N-N=O moiety) and Z (-NOH group is syn to N-N=O moiety) in solution and the coupling constants ruled out the possibility of normal chair conformation. From the theoretical studies and coupling constant values, it was found that all N-nitroso oximes exist as an equilibrium mixture of CA boat conformation (B (1)) and the major isomer was found to be E isomer. The molecular structure of N-nitroso oximes were also determined by semiempirical and Gaussian-03 calculation and the results are in agreement with the experimental studies.