5-(4-甲氧基苯基)-1-甲基吡啶-2(1h)-酮 | 945980-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-(4-甲氧基苯基)-1-甲基吡啶-2(1h)-酮
• 英文名称: 5-(4-methoxyphenyl)-1-methylpyridin-2(1H)-one
• 英文别名: 5-(4-methoxyphenyl)-1-methylpyridin-2-one
• CAS: 945980-20-1
• 化学式: C₁₃H₁₃NO₂
• mdl: MFCD09907673
• 分子量: 215.252
• InChiKey: XRUSRFWOPHJEFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-(4-甲氧基苯基)-1-甲基吡啶-2(1h)-酮 在 氢氧化钾 、 氢溴酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 N-allyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide
  参考文献：
  名称：

  Evaluation of 4′-substituted bicyclic pyridones as non-steroidal inhibitors of steroid 5α-reductase

  摘要：

  4'-Substituted bicyclic pyridones were prepared and evaluated as non-steroidal inhibitors of type I and 2 steroid 5 alpha-reductase (SR). A range of 4'-substituents were incorporated into the bicyclic scaffold to investigate SAR within and across different classes of non-steroidal inhibitors of SR. Bicyclic pyridones containing a 4'-benzoyl or long carbon chain tether showed more potent inhibition against type I SR than inhibitors with N-substituted acetamide groups in the 4'-position. SAR derived from 4'-substituted bicyclic pyridones reported here do not correlate with SAR derived from known potent 4'-substituted biaryl acid SR inhibitors. A 4'-benzoyl group is favoured by the active site in both isozymes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.049
• 作为产物：
  描述：

  2-氟-5-溴吡啶 在 四(三苯基膦)钯 盐酸 、 氢氧化钾 、 四丁基溴化铵 、 lithium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.5h， 生成 5-(4-甲氧基苯基)-1-甲基吡啶-2(1h)-酮
  参考文献：
  名称：

  Evaluation of 4′-substituted bicyclic pyridones as non-steroidal inhibitors of steroid 5α-reductase

  摘要：

  4'-Substituted bicyclic pyridones were prepared and evaluated as non-steroidal inhibitors of type I and 2 steroid 5 alpha-reductase (SR). A range of 4'-substituents were incorporated into the bicyclic scaffold to investigate SAR within and across different classes of non-steroidal inhibitors of SR. Bicyclic pyridones containing a 4'-benzoyl or long carbon chain tether showed more potent inhibition against type I SR than inhibitors with N-substituted acetamide groups in the 4'-position. SAR derived from 4'-substituted bicyclic pyridones reported here do not correlate with SAR derived from known potent 4'-substituted biaryl acid SR inhibitors. A 4'-benzoyl group is favoured by the active site in both isozymes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.049

文献信息

• Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides
  作者：Saurabh Maity、Debapratim Das、Souradip Sarkar、Rajarshi Samanta

  DOI：10.1021/acs.orglett.8b02112

  日期：2018.9.7

  transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.

  开发了一种简单的Pd（II）催化的一般策略，用于使用容易获得的芳基碘化物对2-吡啶酮核心进行C5选择性芳基化。该转化是高度区域选择性的，并且在宽范围和功能基团耐受性下完成。硝酸银在这种直接的位点选择性芳基化中起着至关重要的作用。该方法扩展到合成生物活性分子。
• A General Suzuki Cross-Coupling Reaction of Heteroaromatics Catalyzed by Nanopalladium on Amino-Functionalized Siliceous Mesocellular Foam
  作者：Emma Bratt、Oscar Verho、Magnus J Johansson、Jan-Erling Bäckvall

  DOI：10.1021/jo500409r

  日期：2014.5.2

  Suzuki-Miyaura cross-coupling reactions of heteroaromatics catalyzed by palladium supported in the cavities of amino-functionalized siliceous mesocellular foam are presented. The nanopalladium catalyst effectively couples not only heteroaryl halides with boronic acids but also heteroaryl halides with boronate esters, potassium trifluoroborates, MIDA boronates, and triolborates, producing a wide range of heterobiaryls in good to excellent yields. Furthermore, the heterogeneous palladium nanocatalyst can easily be removed from the reaction mixture by filtration and recycled several times with minimal loss in activity. This catalyst provides an alternative, environmentally friendly, low-leaching process for the preparation of heterobiaryls.
• Asymmetric Homogeneous Hydrogenation of 2-Pyridones
  作者：Frank Glorius、Jędrzej Wysocki、Christoph Schlepphorst

  DOI：10.1055/s-0034-1378703

  日期：——

  An asymmetric homogeneous hydrogenation of 2(1H)-pyridones has been developed, using a ruthenium complex bearing two chiral N-heterocyclic carbene (NHC) ligands. To the best of our knowledge, the presented reaction is the first example of a homogeneous asymmetric conversion of 2-pyridones into the corresponding enantioenriched 2-piperidones.
• Evaluation of 4′-substituted bicyclic pyridones as non-steroidal inhibitors of steroid 5α-reductase
  作者：Anna R. McCarthy、Rolf W. Hartmann、Andrew D. Abell

  DOI：10.1016/j.bmcl.2007.04.049

  日期：2007.7

  4'-Substituted bicyclic pyridones were prepared and evaluated as non-steroidal inhibitors of type I and 2 steroid 5 alpha-reductase (SR). A range of 4'-substituents were incorporated into the bicyclic scaffold to investigate SAR within and across different classes of non-steroidal inhibitors of SR. Bicyclic pyridones containing a 4'-benzoyl or long carbon chain tether showed more potent inhibition against type I SR than inhibitors with N-substituted acetamide groups in the 4'-position. SAR derived from 4'-substituted bicyclic pyridones reported here do not correlate with SAR derived from known potent 4'-substituted biaryl acid SR inhibitors. A 4'-benzoyl group is favoured by the active site in both isozymes. (c) 2007 Elsevier Ltd. All rights reserved.