N-chloroacetyl-3-methyl-2,6-bis(p-chlorophenyl)piperidin-4-one | 1002722-15-7

• 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-methyl-2,6-bis(p-chlorophenyl)piperidin-4-one
• 英文别名: 1-(2-Chloroacetyl)-2,6-bis(4-chlorophenyl)-3-methyl-piperidin-4-one；1-(2-chloroacetyl)-2,6-bis(4-chlorophenyl)-3-methylpiperidin-4-one
• CAS: 1002722-15-7
• 化学式: C₂₀H₁₈Cl₃NO₂
• 分子量: 410.727
• InChiKey: VVZGLJDDTMRIBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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-methyl-2,6-bis(p-chlorophenyl)piperidin-4-one 、 potassium thioacyanate 以 乙腈 为溶剂， 生成 2,6-bis(4-chlorophenyl)-3-methyl-1-(2-thiocyanatoacetyl)piperidin-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
• 作为产物：
  描述：

  4-氯苯甲醛 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-methyl-2,6-bis(p-chlorophenyl)piperidin-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 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.
• 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。