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