N-chloroacetyl-3,5-dimethyl-2,6-bis(p-chlorophenyl)piperidin-4-one | 936097-23-3

• 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-bis(p-chlorophenyl)piperidin-4-one
• 英文别名: 1-(2-Chloroacetyl)-2,6-bis(4-chlorophenyl)-3,5-dimethyl-piperidin-4-one；1-(2-chloroacetyl)-2,6-bis(4-chlorophenyl)-3,5-dimethylpiperidin-4-one
• CAS: 936097-23-3
• 化学式: C₂₁H₂₀Cl₃NO₂
• 分子量: 424.754
• InChiKey: WAYLNDLLDJXKOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 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：

  N-chloroacetyl-3,5-dimethyl-2,6-bis(p-chlorophenyl)piperidin-4-one 、 N-哌嗪甲酸乙酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 以85%的产率得到1-[2-(4-ethoxycarbonylpiperazin-1-yl)acetyl]-3,5-dimethyl-2,6-bis(p-chlorophenyl)piperidin-4-one
  参考文献：
  名称：

  Design and synthesis of novel piperazine unit condensed 2,6-diarylpiperidin-4-one derivatives as antituberculosis and antimicrobial agents

  摘要：

  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.

  DOI：

  10.1007/s00044-011-9573-9
• 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-bis(p-chlorophenyl)piperidin-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

• Synthesis and NMR spectral studies of N-chloroacetyl-2,6-diarylpiperidin-4-ones
  作者：G. Aridoss、S. Balasubramanian、P. Parthiban、S. Kabilan

  DOI：10.1016/j.saa.2007.01.013

  日期：2007.12

  N-chloroacetyl-2,6-diarylpiperidin-4-ones with and without alkyl substituent at C-3 and C-5 (8-14) have also been discussed using the spectral studies. The spectral data and extracted coupling constant values suggest that the compounds 8, 12 and 14 adopt flattened boat conformation whereas the remaining compounds exist in twist-boat conformations in solution with coplanar orientation of the chloroacetyl

  合成了在杂环氮上具有吸电子氯乙酰基的一系列2,6-二芳基哌啶-4-酮。通过一维（（1）H NMR和（13）C NMR）和二维（化合物8和9的HOMOCOSY，NOESY和HSQC光谱，以及仅10种的HOMOCOSY光谱）NMR光谱实现了合成化合物的明确表征数据。还使用光谱研究讨论了在C-3和C-5（8-14）处有或没有烷基取代基的N-氯乙酰基-2,6-二芳基哌啶-4-酮的构象偏好。光谱数据和提取的耦合常数值表明化合物8，图12和14采用扁平的舟状构象，而其余化合物以扭曲舟状构象存在于溶液中，其中杂环氮上存在的氯乙酰基部分共面取向。杂环碳上的氯乙酰基部分的取代基参数也已经根据它们的空间，电子和伽马蚀相互作用进行了推导和详细讨论。氮上的该取代基引起环碳和相关质子的化学位移发生实质性变化。
• Synthesis and antimicrobial activities of N-chloroacetyl-2,6-diarylpiperidin-4-ones
  作者：G. Aridoss、S. Balasubramanian、P. Parthiban、R. Ramachandran、S. Kabilan

  DOI：10.1007/s00044-007-9023-x

  日期：2007.9

  An array of new N-chloroacetyl-2,6-diarylpiperidin-4-ones has been synthesised and their antibacterial activity against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Pseudomonas aeruginosa, and Salmonella typhi, and antifungal activity against Cryptococcus neoformans, Candida albicans, Rhizopus sp., Aspergillus flavus, and Aspergillus niger examined. Compounds 14 against P. aeruginosa, 15 against S. typhi, 16 against S. aureus, and 19 against B. subtilis showed marked antibacterial activity. Similarly, compounds 15 and 19 against A. niger and 19 against A. flavus exerted significant antifungal activities.
• 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 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.