N-(1-oxo-3-phenyl-1-(piperidin-1-yl)-prop-2-en-2-yl)benzamide | 356791-01-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(1-oxo-3-phenyl-1-(piperidin-1-yl)-prop-2-en-2-yl)benzamide
• 英文别名: 1-(α-benzoylamino-trans-cinnamoyl)-piperidine；1-(α-benzoylamino-cis-cinnamoyl)-piperidine；1-(α-Benzoylamino-trans-cinnamoyl)-piperidin；1-(α-Benzoylamino-cis-cinnamoyl)-piperidin；N-(3-oxo-1-phenyl-3-piperidin-1-ylprop-1-en-2-yl)benzamide
• CAS: 356791-01-0
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: BFADWOIEUIYQFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-oxo-3-phenyl-1-(piperidin-1-yl)-prop-2-en-2-yl)benzamide 在 甲酸 作用下， 反应 6.0h， 以91%的产率得到2-benzoylaminocinnamic acid
  参考文献：
  名称：

  2-苯基-4-亚芳基-1,3-恶唑酮与不同亲核试剂的反应合成一些新的杂环

  摘要：

  用丙二腈在干燥的苯中和乙酸铵存在下将1,3-恶唑酮（1a）回流，得到咪唑酮衍生物（2）。然而，在无水乙醇中和在哌啶作为碱的存在下进行相同的反应，得到苯甲酰胺衍生物（4）。将（1a）与对茴香胺融合，得到开放的加合物苯甲酰胺（6），将其在酸性介质中环化，得到咪唑酮衍生物（7）。将咪唑酮（7）与丙二腈一起加热至熔点以上，得到1,3-二氮杂ze衍生物（8）。碳酰肼的反应（9）在乙醇中与靛红得到相应的席夫碱（11），然后与乙酰丙酮，乙酰乙酸乙酯，氰基乙酸乙酯反应，和丙二腈在Ñ丁醇和哌啶，得到苯甲酰胺衍生物（13，14，15）和（16） ， 分别。根据IR，1 H-NMR，质谱和元素分析建立了新合成化合物的结构。

  DOI：

  10.1002/jhet.3419
• 作为产物：
  描述：

  苯甲醛 在 potassium acetate 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 N-(1-oxo-3-phenyl-1-(piperidin-1-yl)-prop-2-en-2-yl)benzamide
  参考文献：
  名称：

  Synthesis and quantitative structure–activity relationships study for phenylpropenamide derivatives as inhibitors of hepatitis B virus replication

  摘要：

  A series of new phenylpropenamide derivatives containing different substituents was synthesized, characterized and evaluated for their anti-hepatitis B virus (HBV) activities. The quantitative structure activity relationships (QSAR) of phenylpropenamide compound have been studied. The 2D-QSAR models, based on OFT and multiple linear regression analysis methods, revealed that higher values of total energy (TE) and lower entropy (S-theta) enhanced the anti-HBV activities of the phenylpropenamide molecules. Predictive 3D-QSAR models were established using SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.032

文献信息

• Phenylpropenamide derivatives: Anti-hepatitis B virus activity of the Z isomer, SAR and the search for novel analogs
  作者：Peiyuan Wang、Devan Naduthambi、Ralph T. Mosley、Congrong Niu、Phillip A. Furman、Michael J. Otto、Michael J. Sofia

  DOI：10.1016/j.bmcl.2011.05.077

  日期：2011.8

  Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t) ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 mu M in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.
• Alkaabi, Sharifa S.; Shawali, Ahmad S., Canadian Journal of Chemistry, 1992, vol. 70, # 10, p. 2515 - 2519
  作者：Alkaabi, Sharifa S.、Shawali, Ahmad S.

  DOI：——

  日期：——
• The Reaction of Azlactones with Secondary Amines
  作者：David K. Barnes、E. Campaigne、R. L. Shriner

  DOI：10.1021/ja01185a030

  日期：1948.5
• Synthesis and quantitative structure–activity relationships study for phenylpropenamide derivatives as inhibitors of hepatitis B virus replication
  作者：Jing Yang、Min Ma、Xue-Ding Wang、Xing-Jun Jiang、Yuan-Yuan Zhang、Wei-Qing Yang、Zi-Cheng Li、Xi-Hong Wang、Bin Yang、Meng-Lin Ma

  DOI：10.1016/j.ejmech.2015.05.032

  日期：2015.6

  A series of new phenylpropenamide derivatives containing different substituents was synthesized, characterized and evaluated for their anti-hepatitis B virus (HBV) activities. The quantitative structure activity relationships (QSAR) of phenylpropenamide compound have been studied. The 2D-QSAR models, based on OFT and multiple linear regression analysis methods, revealed that higher values of total energy (TE) and lower entropy (S-theta) enhanced the anti-HBV activities of the phenylpropenamide molecules. Predictive 3D-QSAR models were established using SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Reaction of 2-Phenyl-4-arylidene-1,3-oxazolones with Different Nucleophiles for Synthesis of Some New Heterocycles
  作者：A. S. A. Youssef、F. A. El-Mariah、F. T. Abd-Elmottaleb、H. E. Hashem

  DOI：10.1002/jhet.3419

  日期：2019.2

  imidazolone derivative (2). However, carrying out the same reaction in absolute ethanol and in the presence of piperidine as a base gave the benzamide derivative (4). Fusion of (1a) with p‐anisidine gave the open adduct benzamide (6), which cyclized in acidic medium to give imidazolone derivative (7). Heating of imidazolone (7) with malononitrile above its melting point afforded 1,3‐diazepine derivative (8)

  用丙二腈在干燥的苯中和乙酸铵存在下将1,3-恶唑酮（1a）回流，得到咪唑酮衍生物（2）。然而，在无水乙醇中和在哌啶作为碱的存在下进行相同的反应，得到苯甲酰胺衍生物（4）。将（1a）与对茴香胺融合，得到开放的加合物苯甲酰胺（6），将其在酸性介质中环化，得到咪唑酮衍生物（7）。将咪唑酮（7）与丙二腈一起加热至熔点以上，得到1,3-二氮杂ze衍生物（8）。碳酰肼的反应（9）在乙醇中与靛红得到相应的席夫碱（11），然后与乙酰丙酮，乙酰乙酸乙酯，氰基乙酸乙酯反应，和丙二腈在Ñ丁醇和哌啶，得到苯甲酰胺衍生物（13，14，15）和（16） ， 分别。根据IR，1 H-NMR，质谱和元素分析建立了新合成化合物的结构。