4-(4-methylphenyl)-6-phenylpyridin-2(1H)-one

• 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: 4-(4-methylphenyl)-6-phenylpyridin-2(1H)-one
• 英文别名: 4-(4-tolyl)-6-phenylpyridin-2-one；6-Phenyl-4-(p-tolyl)pyridin-2(1h)-one；4-(4-methylphenyl)-6-phenyl-1H-pyridin-2-one
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: JEVAVFHACDTJKB-UHFFFAOYSA-N

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：

  4-(4-methylphenyl)-6-phenylpyridin-2(1H)-one 在 氢氧化钾 、 silver carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 2-methyl-6-<<4-(4-methylphenyl)-6-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 4-(4-methylphenyl)-6-phenylpyridin-2(1H)-one
  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

• 一种甲基酮衍生物及其制备方法与应用
  申请人：苏州大学

  公开号：CN106496130B

  公开（公告）日：2019-09-20

  本发明公开了一种甲基酮衍生物及其制备方法与应用，将酮衍生物、有机过氧化物溶于溶剂中，于80‑130℃反应，获得甲基嘧啶酮和甲基吡啶酮衍生物。本发明使用酮衍生物为起始物，原料易得、种类很多；利用本发明的方法得到的产物类型多样，既可以直接使用、又可以用于其他进一步的反应。本发明方法无金属参与，适合于制药工艺。本发明方法路线简短、反应条件温和、反应操作和后处理过程简单、产率较高，适合于规模化生产。
• Metal-free radical C–H methylation of pyrimidinones and pyridinones with dicumyl peroxide
  作者：Pei-Zhi Zhang、Jian-An Li、Ling Zhang、Adedamola Shoberu、Jian-Ping Zou、Wei Zhang

  DOI：10.1039/c6gc03355e

  日期：——

  A new method for free radical methylation of pyrimidinones and pyridinones with dicumyl peroxide (DCP) under metal-free condition is introduced. A 50 g-scale reaction could be performed safely at desired...

  介绍了一种在无金属条件下用过氧化二枯基（DCP）与嘧啶酮和吡啶酮进行自由基甲基化的新方法。50 g规模的反应可以在所需的条件下安全地进行...
• Direct regioselective Csp2–H trifluoromethylation of pyrimidinones and pyridinones
  作者：Pei-Zhi Zhang、Cheng-Kun Li、Guo-Yu Zhang、Ling Zhang、Yao-Jia Jiang、Jian-Ping Zou

  DOI：10.1016/j.tet.2016.04.048

  日期：2016.6

  pyrimidinones and 3-trifluoromethyl pyridinones in moderate to good yields was described. The reaction showed that the steric hindrance due to bulky groups adjacent to the position of attack by the trifluoromethyl radical had important influence on the yield.

  描述了使用CF 3 SO 2 Na / Mn（OAc）3进行嘧啶酮和吡啶酮的直接区域选择性C sp2- H三氟甲基化，以中等至良好的产率提供了5-三氟甲基嘧啶酮和3-三氟甲基吡啶酮。该反应表明，由于三氟甲基自由基的进攻位置附近的庞大基团而引起的位阻对产率有重要影响。
• Mn(OAc)3-Mediated Selective Free Radical Phosphonylation of Pyridinones and Pyrimidinones
  作者：Jian-Ping Zou、Wei Zhang、Wang-Bin Sun、Yun-Fei Ji、Xiang-Qiang Pan、Shao-Fang Zhou、Olayinkataiwo Asekun

  DOI：10.1055/s-0033-1338423

  日期：——

  Abstract The phosphonyl radical generated from the reaction of dimethyl phosphite with manganese(III) acetate adds selectively to the 3-position of pyridin-2-ones or the 5-position of pyrimidin-4-ones to afford phosphonylated products in good yields. The phosphonyl radical generated from the reaction of dimethyl phosphite with manganese(III) acetate adds selectively to the 3-position of pyridin-2-ones

  摘要 由亚磷酸二甲酯与乙酸锰（III）反应生成的膦酰基基团选择性地加到吡啶-2-酮的3-位或嘧啶-4-酮的5-位上，从而以高收率得到膦酰化产物。 由亚磷酸二甲酯与乙酸锰（III）反应生成的膦酰基基团选择性地加到吡啶-2-酮的3-位或嘧啶-4-酮的5-位上，从而以高收率得到膦酰化产物。
• Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones: novel access to 2,4,6-triaryl pyridines
  作者：Rajni Khajuria、Prakash Kannaboina、Kamal K. Kapoor、Annah Gupta、Gaurav Raina、Amanpreet Kaur Jassal、Love Karan Rana、Maninder S. Hundal、Parthasarathi Das

  DOI：10.1039/c5ob00545k

  日期：——

  A wide range of 4,6-diarylated-2(1H)-one derivatives were synthesized in excellent yields from chalcones in one pot. Further the designed 4,6-diarylated pyridin-2(1H)-one derivatives have been successfully utilized in synthesizing 2,4,6-triarylpyridines.

  一种广泛的4,6-二芳基-2（1H）-酮衍生物从查尔酮中一锅法合成，收率极高。此外，设计的4,6-二芳基吡啶-2（1H）-酮衍生物已成功用于合成2,4,6-三芳基吡啶。