1-allyl-2,6-diphenylpiperidin-4-one

• 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: 1-allyl-2,6-diphenylpiperidin-4-one
• 英文别名: 2,6-Diphenyl-1-prop-2-enylpiperidin-4-one；2,6-diphenyl-1-prop-2-enylpiperidin-4-one
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: ZKQFGVRAOKOGKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-allyl-2,6-diphenylpiperidin-4-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以83%的产率得到1-allyl-2,6-diphenylpiperidin-4-one oxime
  参考文献：
  名称：

  Design, synthesis, spectral and biological evaluation of novel 1-allyl substituted 2,6-diphenylpiperidin-4-ones and its derivatives of oximes/oxime ethers

  摘要：

  A series of 1-allyl-2,6-diphenylpiperidin-4-one oximes 17-24 and 1-allyl-2,6-diphenylpiperidin-4-one O-benzyloximes 25-32 were synthesized from respective 1-allyl-2,6-diphenylpiperidin-4-ones 9-16. The structure and the conformations have been investigated for all the synthesized compounds 9-32 by analytical and spectral techniques (IR, Mass, 1H, 13C, 2D NMR and X-ray Diffraction). Based on the proton NMR analysis, all the synthesized compounds 9-32, exposed chair conformation except compounds 22 and 30 (twist boat conformation). For all the synthesized compounds 9-32 antimicrobial activity has been carried out against a panel of selected bacterial and fungal strains using Streptomycin and Amphotericin B as standards. Antibacterial and antifungal activity of compounds 19, 21, 23 (allyl oximes) 25-29, 31, 32 (allyl oxime ethers) and 11, 13 (ketones) exerted moderate to excellent activity against Staphylococcus aureus, Bacillus subtilis, Salmonella typhi bacterial strains and Penicillium chrysogenum, Aspergillus niger, Fusarium oxysporum fungal strains. The MIC results of all the synthesized compounds revealed that most of the oxime ether compounds exhibit excellent activity against selected bacterial and fungal strains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.002
• 作为产物：
  描述：

  苯甲醛 在 ammonium acetate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 1-allyl-2,6-diphenylpiperidin-4-one
  参考文献：
  名称：

  Design, synthesis, spectral and biological evaluation of novel 1-allyl substituted 2,6-diphenylpiperidin-4-ones and its derivatives of oximes/oxime ethers

  摘要：

  A series of 1-allyl-2,6-diphenylpiperidin-4-one oximes 17-24 and 1-allyl-2,6-diphenylpiperidin-4-one O-benzyloximes 25-32 were synthesized from respective 1-allyl-2,6-diphenylpiperidin-4-ones 9-16. The structure and the conformations have been investigated for all the synthesized compounds 9-32 by analytical and spectral techniques (IR, Mass, 1H, 13C, 2D NMR and X-ray Diffraction). Based on the proton NMR analysis, all the synthesized compounds 9-32, exposed chair conformation except compounds 22 and 30 (twist boat conformation). For all the synthesized compounds 9-32 antimicrobial activity has been carried out against a panel of selected bacterial and fungal strains using Streptomycin and Amphotericin B as standards. Antibacterial and antifungal activity of compounds 19, 21, 23 (allyl oximes) 25-29, 31, 32 (allyl oxime ethers) and 11, 13 (ketones) exerted moderate to excellent activity against Staphylococcus aureus, Bacillus subtilis, Salmonella typhi bacterial strains and Penicillium chrysogenum, Aspergillus niger, Fusarium oxysporum fungal strains. The MIC results of all the synthesized compounds revealed that most of the oxime ether compounds exhibit excellent activity against selected bacterial and fungal strains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.002

文献信息

• An imino-Diels–Alder route to meso-2,6-disubstituted-4-piperidones
  作者：Ana-Belén Garcı́a、Carlos Valdés、Marı́a-Paz Cabal

  DOI：10.1016/j.tetlet.2004.03.195

  日期：2004.5

  A convenient stereoselective preparation of meso-2,6-disubstituted-4-piperidones has been developed by imino-Diels–Alder reaction of 2-amino-1,3-butadienes with imines in the presence of catalytic amount of Cu(TfO)2.

  的一种方便的立体选择性制备内消旋-2,6-二取代-4-哌啶酮已经通过与亚胺在铜（TFO）的催化量存在的2-氨基-1,3-丁二烯亚氨基Diels-Alder反应研制2。
• Stereoselective Synthesis of <i>meso</i>- and <i>cis</i>-2,6-Diarylpiperidin-4-ones Catalyzed by <scp>l</scp>-Proline
  作者：Fernando Aznar、Ana-Belén García、Noelia Quiñones、María-Paz Cabal

  DOI：10.1055/s-2007-990814

  日期：2008.2

  A convenient stereoselective preparation of meso- and cis-2,6-diarylpiperidin-4-ones has been developed by aza-Diels-Alder reaction­ catalyzed by l-proline from simple and commercially available starting materials.

  在 l-脯氨酸的催化下，利用简单的市售起始原料，通过偶氮-Diels-Alder 反应，开发出了一种方便的立体选择性制备介-和顺-2,6-二芳基哌啶-4-酮的方法。
• Design, synthesis, spectral and biological evaluation of novel 1-allyl substituted 2,6-diphenylpiperidin-4-ones and its derivatives of oximes/oxime ethers
  作者：Kuppusamy Narayanan、Mani Shanmugam、Sarangan Jothivel、Senthamaraikannan Kabilan

  DOI：10.1016/j.bmcl.2012.09.002

  日期：2012.11

  A series of 1-allyl-2,6-diphenylpiperidin-4-one oximes 17-24 and 1-allyl-2,6-diphenylpiperidin-4-one O-benzyloximes 25-32 were synthesized from respective 1-allyl-2,6-diphenylpiperidin-4-ones 9-16. The structure and the conformations have been investigated for all the synthesized compounds 9-32 by analytical and spectral techniques (IR, Mass, 1H, 13C, 2D NMR and X-ray Diffraction). Based on the proton NMR analysis, all the synthesized compounds 9-32, exposed chair conformation except compounds 22 and 30 (twist boat conformation). For all the synthesized compounds 9-32 antimicrobial activity has been carried out against a panel of selected bacterial and fungal strains using Streptomycin and Amphotericin B as standards. Antibacterial and antifungal activity of compounds 19, 21, 23 (allyl oximes) 25-29, 31, 32 (allyl oxime ethers) and 11, 13 (ketones) exerted moderate to excellent activity against Staphylococcus aureus, Bacillus subtilis, Salmonella typhi bacterial strains and Penicillium chrysogenum, Aspergillus niger, Fusarium oxysporum fungal strains. The MIC results of all the synthesized compounds revealed that most of the oxime ether compounds exhibit excellent activity against selected bacterial and fungal strains. (C) 2012 Elsevier Ltd. All rights reserved.