N-chloroacetyl-3-ethyl-2,6-diphenylpiperidin-4-one | 936097-20-0

• 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: N-chloroacetyl-3-ethyl-2,6-diphenylpiperidin-4-one
• 英文别名: N-chloroacetyl-r-2,c-6-diphenyl-t-3-ethylpiperidin-4-one；1-(2-Chloroacetyl)-3-ethyl-2,6-diphenylpiperidin-4-one
• CAS: 936097-20-0
• 化学式: C₂₁H₂₂ClNO₂
• 分子量: 355.864
• InChiKey: CFIXPSAKWPBDDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  咪唑 、 N-chloroacetyl-3-ethyl-2,6-diphenylpiperidin-4-one 在 三乙胺 作用下， 以68%的产率得到1-[2-(1H-imidazol-1-yl)acetyl]-3-ethyl-2,6-diphenylpiperidin-4-one
  参考文献：
  名称：

  咪唑/苯并三唑取代的哌啶-4-酮衍生物的合成，光谱，晶体结构和体外抗菌评估

  摘要：

  已合成了咪唑/苯并三唑类似物取代的哌啶-4-一衍生物（17-26）。通过IR，1 H NMR，13 C NMR和质谱分析对它们的化学结构进行表征。另外，还已经记录了化合物21和23的单晶X射线衍射。合成的化合物具有针对病原性微生物菌株的体外抗菌和抗真菌活性。结果指出，针对枯草芽孢杆菌的化合物19和24和针对大肠杆菌的化合物20和24 探索了优异的抑制活性。

  DOI：

  10.1016/j.ejmech.2011.02.036
• 作为产物：
  描述：

  苯甲醛 在 ammonium acetate 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.0h， 生成 N-chloroacetyl-3-ethyl-2,6-diphenylpiperidin-4-one
  参考文献：
  名称：

  3-烷基-2,6-二芳基哌啶-4-酮的N-硫氰基乙酰基衍生物的化学选择性合成和光谱研究

  摘要：

  图形摘要 摘要 3-烷基-2,6-二芳基哌啶-4-酮的一系列N-硫氰酸根合乙酰基衍生物已通过各自哌啶-4-酮的N-氯乙酰衍生物与中间硫氰酸酯亲核试剂之间的反应合成。合成的化合物已通过 FT-IR、1H、13C、1H-1H COSY、1H-13C COSY 和 NOESY 光谱进行表征。光谱数据揭示了六元杂环的构象优先级。

  DOI：

  10.1080/10426507.2016.1149852

文献信息

• Synthesis, stereochemistry and antimicrobial evaluation of some N-morpholinoacetyl-2,6-diarylpiperidin-4-ones
  作者：G. Aridoss、S. Balasubramanian、P. Parthiban、S. Kabilan

  DOI：10.1016/j.ejmech.2006.12.005

  日期：2007.6

  Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi and antifungal activity against Candida albicans, Rhizopus sp., Aspergillus niger and Aspergillus flavus were evaluated. Structure and stereochemistry of all the N-morpholinoacetyl-2,6-diarylpiperidin-4-ones have been analyzed using (1)H and (13)C NMR spectroscopic techniques. In all the cases, amide N-CO group is preferentially in coplanar orientation

  为寻找有效的抗菌剂新途径，合成了一系列新型N-吗啉代乙酰基-2,6-二芳基哌啶-4-酮，它们对金黄色葡萄球菌，大肠杆菌，铜绿假单胞菌和鼠伤寒沙门氏菌和评估了对白色念珠菌，根霉菌，黑曲霉和黄曲霉的抗真菌活性。所有的N-吗啉代乙酰基-2,6-二芳基哌啶-4-酮的结构和立体化学已使用（1）H和（13）C NMR光谱技术进行了分析。在所有情况下，相对于哌啶酮环的动态平均平面，酰胺N-CO基团优选处于共面取向。此外，所有对称取代的化合物19、23、24，预期26和27将采用半舟构型，而其他化合物20-22和25将采用扭转舟构型。这九种化合物的结构活性关系结果表明，化合物26和27对除27种抗金黄色葡萄球菌外的所有细菌菌株均具有优异的抗菌活性。对白色念珠菌和黄曲霉，化合物24表现出优异的抗真菌活性，而对根霉属（Rhizopus sp。）而言，化合物25显示出强效活性。获得的结果可以用作构建具有与标准药
• Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: Antimicrobial, analgesic and antipyretic studies
  作者：G. Aridoss、P. Parthiban、R. Ramachandran、M. Prakash、S. Kabilan、Yeon Tae Jeong

  DOI：10.1016/j.ejmech.2008.03.031

  日期：2009.2

  A series of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones (13c-21c) were synthesized by the base catalyzed nucleophilic substitution of N-chloroacetyl-2,6-diarylpiperidin-4-ones obtained from their corresponding 2,6-diarylpiperidin-4-ones with N-methylpiperazine. These newly synthesized compounds were characterized by one- and two-dimensional NMR spectral studies. In all the cases, the piperazine ring adopted normal chair conformation with equatorial orientation of methyl group irrespective of the non-chair conformations of the piperidin-4-one moiety. All the compounds were screened for their possible antibacterial and antifungal activities against a spectrum of microbial agents besides analgesic and antipyretic activities. These biological studies proved that compounds 17c/18c against bacterial and 18c/20c against fungal strains exhibited promising antimicrobial activities whereas 17c/19c and 18c/19c showed beneficial analgesic and antipyretic profiles, respectively, at a concentration of 60 mg/kg and were also found to be more potent than the reference drug. (C) 2008 Elsevier Masson SAS. All fights reserved.
• Synthesis, conformational preferences and antimicrobial evaluation of N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones
  作者：A. Akila、P. Jeganathan、S. Ponnuswamy

  DOI：10.1016/j.molstruc.2016.05.028

  日期：2016.9

  Five new N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones 11-15 have been synthesized and characterized using IR, H-1, C-13, DEPT & 2D NMR and mass spectral studies. The NMR spectral data indicate that the N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones 11-15 prefer to exist in an equilibrium between B1 and B2 conformations. Furthermore, the antibacterial and antifungal studies were carried out. The results show that the piperazinoacetyl piperidin-4-ones 11-15 exhibit good activity against the selected bacterial and fungal strains. (C) 2016 Elsevier B.V. All rights reserved.
• Design and synthesis of novel piperazine unit condensed 2,6-diarylpiperidin-4-one derivatives as antituberculosis and antimicrobial agents
  作者：Mannangatty Rani、Paramasivam Parthiban、Rajamanickam Ramachandran、Senthamaraikannan Kabilan

  DOI：10.1007/s00044-011-9573-9

  日期：2012.5

  A new series of 1-[2-(4-ethoxycarbonylpiperazine-1-yl)acetyl]-2,6-diarylpiperidin-4-ones (3a-3j) has been synthesized by conventional method and were characterized by IR, elemental analysis, mass spectral, 1 H NMR, C-13 NMR, and single crystal X-ray diffraction analysis. The synthesized compounds were evaluated for their antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC-27294) and also its antimicrobial activity were examined against five familiar bacterial and fungal strains. Among the synthesized compounds, compounds 3e-3j exhibit higher inhibition potency (16 mu g/ml) against M. tuberculosis H37Rv. Furthermore, compounds containing fluoro substituent in the phenyl ring at C-2 and C-6 positions of the piperidin-4-one motif (compounds 3c, 3d, and 3i) exerted better antibacterial and antifungal activity than the other phenyl-substituted compounds.
• Synthesis of Novel N‐Morpholinoacetyl‐2,6‐diarylpiperidin‐4‐ones
  作者：G. Aridoss、S. Balasubramanian、P. Parthiban、S. Kabilan

  DOI：10.1080/00397910601163828

  日期：2007.3.1

  A series of N-chloroacetyl-2,6-diarylpiperidin-4-ones (10-18) obtained from the corresponding 2,6-diarylpiperidin-4-ones upon base-catalyzed condensation with morpholine afforded N-morpholinoacetyl-2,6-diarylpiperidin-4-ones (19-27). The synthesized compounds have been characterized by their elemental, analytical, and spectral data.