1-(4-Acetylphenyl)piperidin-4-on | 79421-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-Acetylphenyl)piperidin-4-on
• 英文别名: 1-(4-Acetylphenyl)piperidin-4-one
• CAS: 79421-48-0
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: DXTNVVBYDATEFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-Acetylphenyl)piperidin-4-on 在 Hg(II)-EDTA 作用下， 以 水 为溶剂， 反应 5.0h， 以35%的产率得到1-(4-Acetylphenyl)-2,3-dihydro-1H-pyridin-4-on
  参考文献：
  名称：

  1,3-Dioxolane von N-substituierten 4-Piperidonen als Dehydrierungssubstrat / 1,3-Dioxolanes of N-Substituted 4-Piperidones as Substrates for Dehydrogenations

  摘要：

  本文研究了使用缬氨酸汞脱氢反应掩蔽N-三级4-哌啶酮中的羰基的甲缩醛的适用性。不同的1,3-二氧杂环烷根据N-取代基表现出不同的行为。使用简单的脂肪基主要获得脱氢但水解产物。这些烯酮也可以从相应的4-哌啶酮的脱氢反应中得到。对于带有邻位参与的芳基取代基，类似的情况也发生了，但产率较低。带有邻位参与的芳基取代基在一定程度上保留了甲缩醛结构，产生了不同的氧化产物。

  DOI：

  10.1515/znb-1997-0115
• 作为产物：
  描述：

  1-[4-(1,4-二氧杂-8-氮杂螺[4.5]癸烷-8-基)苯基]乙酮 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 120.0h， 以87%的产率得到1-(4-Acetylphenyl)piperidin-4-on
  参考文献：
  名称：

  1,3-Dioxolane von N-substituierten 4-Piperidonen als Dehydrierungssubstrat / 1,3-Dioxolanes of N-Substituted 4-Piperidones as Substrates for Dehydrogenations

  摘要：

  本文研究了使用缬氨酸汞脱氢反应掩蔽N-三级4-哌啶酮中的羰基的甲缩醛的适用性。不同的1,3-二氧杂环烷根据N-取代基表现出不同的行为。使用简单的脂肪基主要获得脱氢但水解产物。这些烯酮也可以从相应的4-哌啶酮的脱氢反应中得到。对于带有邻位参与的芳基取代基，类似的情况也发生了，但产率较低。带有邻位参与的芳基取代基在一定程度上保留了甲缩醛结构，产生了不同的氧化产物。

  DOI：

  10.1515/znb-1997-0115

文献信息

• A Convenient Synthesis of 1-Aryl-4-piperidones
  作者：Edward C. Taylor、Jerauld S. Skotnicki

  DOI：10.1055/s-1981-29539

  日期：——
• First‐in‐class pyrido[2,3‐ <i>d</i> ]pyrimidine‐2,4(1 <i>H</i> ,3 <i>H</i> )‐diones against leishmaniasis and tuberculosis: Rationale, in vitro, ex vivo studies and mechanistic insights
  作者：Deepthi Ramesh、Deblina Sarkar、Annu Joji、Monica Singh、Amaresh K. Mohanty、Balaji G. Vijayakumar、Mitali Chatterjee、Dharmarajan Sriram、Suresh K. Muthuvel、Tharanikkarasu Kannan

  DOI：10.1002/ardp.202100440

  日期：2022.4

  AbstractPyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones were synthesized, for the first time, from indole chalcones and 6‐aminouracil, and their ability to inhibit leishmaniasis and tuberculosis (Tb) infections was evaluated. The in vitro antileishmanial activity against promastigotes of Leishmania donovani revealed exceptional activities of compounds 3, 12 and 13, with IC50 values ranging from 10.23 ± 1.50 to 15.58 ± 1.67 µg/ml, which is better than the IC50 value of the standard drug pentostam of 500 μg/ml. The selectivity of the compounds towards Leishmania parasites was evaluated via ex vivo studies in Swiss albino mice. The efficiency of these compounds against Tb infection was then evaluated using the in vitro anti‐Tb microplate Alamar Blue assay. Five compounds, 3, 7, 8, 9 and 12, showed MIC100 values against the Mycobacterium tuberculosis H37Rv strain at 25 µg/ml, and compound 20 yielded an MIC100 value of 50 µg/ml. Molecular modelling of these compounds highlighted interactions with binding sites of dihydrofolate reductase, pteridine reductase and thymidylate kinase, thus establishing the rationale of their pharmacological activity against both pathogens, which is consistent with the in vitro results. From the above results, it is clear that compounds 3 and 12 are promising lead candidates for Leishmania and Mycobacterium infections and may be promising for coinfections.
• TAYLOR, E. C.;SKOTNICKI, J. S., SYNTHESIS, BRD, 1981, N 8, 606-608
  作者：TAYLOR, E. C.、SKOTNICKI, J. S.

  DOI：——

  日期：——
• 1,3-Dioxolane von N-substituierten 4-Piperidonen als Dehydrierungssubstrat / 1,3-Dioxolanes of N-Substituted 4-Piperidones as Substrates for Dehydrogenations
  作者：H. Möhrle、M. Jeandrée

  DOI：10.1515/znb-1997-0115

  日期：1997.1.1

  The applicability of ketals was examined for masking the carbonyl group in N-tertiary 4-piperidones during the dehydrogenation using mercury-edta. Various 1,3-dioxolanes showed a different behaviour in dependence on the N-substituent. With simple aliphatic moieties mainly dehydrogenated but hydrolyzed products were received. These enaminones were also available from the dehydrogenations of the corresponding 4-piperidones. Similar applied to para-acyl-aromatic substituted derivatives but with less yields. Aromatic substituents bearing a neighbour group on ortho-position with participation gave rise to different oxidation products partially with preservation of the ketal structure

  本文研究了使用缬氨酸汞脱氢反应掩蔽N-三级4-哌啶酮中的羰基的甲缩醛的适用性。不同的1,3-二氧杂环烷根据N-取代基表现出不同的行为。使用简单的脂肪基主要获得脱氢但水解产物。这些烯酮也可以从相应的4-哌啶酮的脱氢反应中得到。对于带有邻位参与的芳基取代基，类似的情况也发生了，但产率较低。带有邻位参与的芳基取代基在一定程度上保留了甲缩醛结构，产生了不同的氧化产物。