(NE)-N-[2,6-bis(4-methoxyphenyl)-3-methylpiperidin-4-ylidene]hydroxylamine

• 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: (NE)-N-[2,6-bis(4-methoxyphenyl)-3-methylpiperidin-4-ylidene]hydroxylamine
• 化学式: C₂₀H₂₄N₂O₃
• 分子量: 340.422
• InChiKey: OYGRPLURZDNYIE-RELWKKBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  63.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (NE)-N-[2,6-bis(4-methoxyphenyl)-3-methylpiperidin-4-ylidene]hydroxylamine 、 3-溴丙炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以85%的产率得到(E)-2,6-bis(4-methoxyphenyl)-3-methyl-1-(prop-2-yn-1-yl)piperidin-4-one oxime
  参考文献：
  名称：

  Synthesis, characterization, computational calculation and biological studies of some 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oxime derivatives

  摘要：

  A new series of 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oximes (17-24) were designed and synthesized from 2,6-diarylpiperidin-4-one oximes (9-16) with propargyl bromide. Unambiguous structural elucidation has been carried out by investigating IR, NMR (H-1, C-13, H-1-H-1 COSY and HSQC), mass spectral techniques and theoretical (DFT) calculations. Further, crystal structure of compound 17 was evaluated by single crystal X-ray diffraction analysis. Single crystal X-ray structural analysis of compound 17 evidenced that the configuration about C=N double bond is syn to C-5 carbon (E-form). The existence of chair conformation was further confirmed by theoretical DFT calculation. All the synthesized compounds were screened for in vitro antimicrobial activity against a panel of selected bacterial and fungal strains using Ciprofloxacin and Ketoconazole as standards. The minimum inhibition concentration (MIC) results revealed that most of the 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oximes (17, 19, 20 and 23) exhibited better activity against the selected bacterial and fungal strains. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.12.014
• 作为产物：
  描述：

  2,6-双(4-甲氧基苯基)-3-甲基哌啶-4-酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (NE)-N-[2,6-bis(4-methoxyphenyl)-3-methylpiperidin-4-ylidene]hydroxylamine
  参考文献：
  名称：

  Synthesis, characterization, computational calculation and biological studies of some 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oxime derivatives

  摘要：

  A new series of 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oximes (17-24) were designed and synthesized from 2,6-diarylpiperidin-4-one oximes (9-16) with propargyl bromide. Unambiguous structural elucidation has been carried out by investigating IR, NMR (H-1, C-13, H-1-H-1 COSY and HSQC), mass spectral techniques and theoretical (DFT) calculations. Further, crystal structure of compound 17 was evaluated by single crystal X-ray diffraction analysis. Single crystal X-ray structural analysis of compound 17 evidenced that the configuration about C=N double bond is syn to C-5 carbon (E-form). The existence of chair conformation was further confirmed by theoretical DFT calculation. All the synthesized compounds were screened for in vitro antimicrobial activity against a panel of selected bacterial and fungal strains using Ciprofloxacin and Ketoconazole as standards. The minimum inhibition concentration (MIC) results revealed that most of the 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oximes (17, 19, 20 and 23) exhibited better activity against the selected bacterial and fungal strains. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.12.014

文献信息

• Synthesis, characterization, computational calculation and biological studies of some 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oxime derivatives
  作者：G. Sundararajan、D. Rajaraman、T. Srinivasan、D. Velmurugan、K. Krishnasamy

  DOI：10.1016/j.saa.2014.12.014

  日期：2015.3

  A new series of 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oximes (17-24) were designed and synthesized from 2,6-diarylpiperidin-4-one oximes (9-16) with propargyl bromide. Unambiguous structural elucidation has been carried out by investigating IR, NMR (H-1, C-13, H-1-H-1 COSY and HSQC), mass spectral techniques and theoretical (DFT) calculations. Further, crystal structure of compound 17 was evaluated by single crystal X-ray diffraction analysis. Single crystal X-ray structural analysis of compound 17 evidenced that the configuration about C=N double bond is syn to C-5 carbon (E-form). The existence of chair conformation was further confirmed by theoretical DFT calculation. All the synthesized compounds were screened for in vitro antimicrobial activity against a panel of selected bacterial and fungal strains using Ciprofloxacin and Ketoconazole as standards. The minimum inhibition concentration (MIC) results revealed that most of the 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oximes (17, 19, 20 and 23) exhibited better activity against the selected bacterial and fungal strains. (C) 2014 Elsevier B.V. All rights reserved.