2(1H)-Pyridinone, 6-(4-methylphenyl)-4-phenyl- | 143969-10-2

• 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
• 英文名称: 2(1H)-Pyridinone, 6-(4-methylphenyl)-4-phenyl-
• 英文别名: 6-(4-methylphenyl)-4-phenyl-1H-pyridin-2-one
• CAS: 143969-10-2
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: WVGGRNICFAPFKX-UHFFFAOYSA-N

物化性质

• 熔点：
  226-228 °C
• 沸点：
  516.7±50.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2(1H)-Pyridinone, 6-(4-methylphenyl)-4-phenyl- 在 氢氧化钾 、 silver carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 38.0h， 生成 6-<<6-(4-methylphenyl)-4-phenyl-2-pyridyl>oxy>hexanoic acid
  参考文献：
  名称：

  .omega.-[(4,6-Diphenyl-2-pyridyl)oxy]alkanoic acid derivatives: a new family of potent and orally active LTB4 antagonists

  摘要：

  A series of omega-[(4,6-diphenyl-2-pyridyl)oxy]alkanoic acid derivatives was prepared which inhibited the binding of leukotriene B4 to its receptors on guinea pig spleen membranes and on human polymorphonuclear leukocytes (PMNs) and selectively antagonized the LTB4-induced elastase release in human PMNs. On the basis of these three screens, a structure-activity relationship was investigated. Alpha-Substitution on the carboxylic acid side chain led to only small changes in the binding affinities but greatly enhanced the LTB4 antagonist activity. Substitution on the phenyl rings was also evaluated. The terminal carboxylic acid function can be replaced by a tetrazole ring without loss in activity. The beat in vitro LTB4 antagonists of this series were investigated in vivo in the inhibition of LTB4-induced leukopenia in rabbits. Compound 9b (RP69698) displayed potent LTB4 antagonist activity, after oral administration, with an ED50 value of 6.7 mg/kg.

  DOI：

  10.1021/jm00101a008
• 作为产物：
  描述：

  1-(4-甲基苯基)-3-苯基-1,3-丙烷二酮 在 乙醇 、 硫酸 、 二乙胺 、 氰乙酰胺 作用下， 生成 2(1H)-Pyridinone, 6-(4-methylphenyl)-4-phenyl-
  参考文献：
  名称：

  Basu, Journal of the Indian Chemical Society, 1930, vol. 7, p. 815,823

  摘要：

  DOI：

文献信息

• Three‐Component Castagnoli‐Cushman Reaction of 3‐Arylglutaconic Acid Anhydrides, Carbonyl Compounds, and Ammonium Acetate: a Quick and Flexible Way to Assemble Polysubstituted <i>NH</i> ‐δ‐lactams
  作者：Anatoly A. Peshkov、Olga Bakulina、Dmitry Dar'in、Grigory Kantin、Anton Bannykh、Vsevolod A. Peshkov、Mikhail Krasavin

  DOI：10.1002/ejoc.202001617

  日期：2021.3.19

  Three‐component Castagnoli‐Cushman reaction of 3‐arylglutaconic anhydrides with carbonyl compound and ammonium acetate delivers medicinally important NH‐δ‐lactams. The scope of the protocol has been thoroughly explored paying particular attention to the carbonyl component using wide array of aliphatic and aromatic aldehydes as well as rarely involved cyclic and acyclic ketones.

  3-芳基戊二酸酐与羰基化合物和乙酸铵的三组分Castagnoli-Cushman反应产生了医学上重要的NH -δ-内酰胺。已经彻底探索了方案的范围，特别注意使用多种脂族和芳族醛以及很少涉及的环状和非环状酮对羰基组分的关注。
• Barat, Journal of the Indian Chemical Society, 1930, vol. 7, p. 851,859
  作者：Barat

  DOI：——

  日期：——
• Barat, Journal of the Indian Chemical Society, 1930, vol. 7, p. 321,333
  作者：Barat

  DOI：——

  日期：——
• Wang, Shaozhong; Yu, Gang; Lu, Jun, Synthesis, 2003, # 4, p. 487 - 490
  作者：Wang, Shaozhong、Yu, Gang、Lu, Jun、Xiao, Kun、Hu, Yuefei、Hu, Hongwen

  DOI：——

  日期：——
• Benzotriazole-Assisted Preparations of 2-(Substituted amino)pyridines and Pyrid-2-ones
  作者：Alan R. Katritzky、Sergei A. Belyakov、Alexander E. Sorochinsky、Scott A. Henderson、Jie Chen

  DOI：10.1021/jo970561h

  日期：1997.9.1

  Base-promoted reactions of benzotriazolyl-containing acetic acid derivatives, 2-(benzotriazol-1-yl)acetonitrile (7a), 2-(benzotriazol-1-yl)acetamide (7b), and (+/-)-2-(benzotriazol-1-yl)propionamide (7c), with alpha,beta-unsaturated ketones 8 give efficient and regioselective access to previously difficult to attain 3-unsubstituted pyridine derivatives: the 2-(substituted amino)pyridines 14a-k and the 4,6-substituted pyrid-2-ones 15a-h. The pyridine rings result from tandem [3 + 3] annulations involving a Michael addition followed by cyclization.