N-chloroacetyl-3,5-dimethyl-2,6-diphenylpiperidin-4-one | 936097-22-2

• 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-3,5-dimethyl-2,6-diphenylpiperidin-4-one
• 英文别名: 1-(2-Chloroacetyl)-3,5-dimethyl-2,6-diphenylpiperidin-4-one
• CAS: 936097-22-2
• 化学式: C₂₁H₂₂ClNO₂
• 分子量: 355.864
• InChiKey: VFAZYGRLPLNCKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 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-3,5-dimethyl-2,6-diphenylpiperidin-4-one 在 三乙胺 作用下， 以75%的产率得到1-[2-(1H-imidazol-1-yl)acetyl]-3,5-dimethyl-2,6-diphenyl-piperidin-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：

  3-戊酮 在 ammonium acetate 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 生成 N-chloroacetyl-3,5-dimethyl-2,6-diphenylpiperidin-4-one
  参考文献：
  名称：

  某些N-吗啉代乙酰基2,6-二芳基哌啶-4-酮的合成，立体化学和抗菌性评估。

  摘要：

  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

  DOI：

  10.1016/j.ejmech.2006.12.005

文献信息

• Chemoselective synthesis and spectral studies of <i>N</i>-thiocyanatoacetyl derivatives of 3-alkyl-2,6-diarylpiperidin-4-ones
  作者：M. Velayutham Pillai、K. Rajeswari、C. Udhaya Kumar、C. Ramalingan、A. Manohar、T. Vidhyasagar

  DOI：10.1080/10426507.2016.1149852

  日期：2016.9.1

  of the respective piperidin–4–ones and the ambident thiocyanate nucleophile. The synthesized compounds have been characterized through FT–IR, 1H, 13C, 1H–1H COSY, 1H–13C COSY and NOESY spectra. The spectral data reveal the conformational priority of the six-membered heterocyclic ring.

  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。
• 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.