1-methyl-3-phenylpyridin-2(1H)-one | 13180-21-7

• 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: 1-methyl-3-phenylpyridin-2(1H)-one
• 英文别名: 1-methyl-3-phenyl-2(1H)-pyridone；1-Methyl-3-phenylpyridin-2-one
• CAS: 13180-21-7
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: ULYZWTLDAJORNL-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  382.7±31.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-3-phenylpyridin-2(1H)-one 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 、 lithium chloride 作用下， 以 乙醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 33.0h， 生成 1-methyl-5-[4-[3-[(2R)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-3-phenylpyridin-2-one
  参考文献：
  名称：

  Synthesis and evaluation of pyridone-phenoxypropyl-R-2-methylpyrrolidine analogues as histamine H3 receptor antagonists

  摘要：

  6-{4-[3-(R)-2-Methylpyrrolidin-1-yl) propoxy]-phenyl}-2H-pyridazin-3-one 6 (Irdabisant; CEP-26401) was recently reported as a potent H3R antagonist with excellent drug-like properties and in vivo activity that advanced into clinical evaluation. A series of pyridone analogs of 6 was synthesized and evaluated as H3R antagonists. Structure-activity relationships revealed that the 5-pyridone regiomer was optimal for H3R affinity. N-Methyl 9b showed excellent H3R affinity, acceptable pharmacokinetics and pharmaceutical properties. In vivo evaluation of 9b showed potent activity in the rat dipsogenia model and robust wake-promoting activity in the rat EEG model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.091
• 作为产物：
  描述：

  3-溴-2-氯吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 2-甲基-2-丁醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 74.0h， 生成 1-methyl-3-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  Asymmetric Homogeneous Hydrogenation of 2-Pyridones

  摘要：

  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.

  DOI：

  10.1055/s-0034-1378703

文献信息

• A directing group free Pd(<scp>ii</scp>)-catalysed desulfitative C6-arylation of 2-pyridone using an arylsulfonyl chloride
  作者：Ujjwal Karmakar、Rajarshi Samanta

  DOI：10.1039/d0ob01716g

  日期：——

  A Pd(II)-catalysed direct desulfitative arylation was realized at the C6-position of the 2-pyridone scaffold. Aryl sulfonyl chloride was used as an alternative arylating agent. The required site-selectivity occurred without the strategic installation of a heteroatom containing directing group. Preliminary mechanistic studies revealed that radical species were involved during this process.

  在 2-吡啶酮支架的 C6 位实现了Pd( II ) 催化的直接脱硫芳基化。芳基磺酰氯用作替代的芳基化剂。在没有战略性地安装含杂原子的导向基团的情况下，就可以实现所需的位点选择性。初步机制研究表明，在此过程中涉及自由基物种。
• Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions
  作者：Parul Chauhan、Makthala Ravi、Shikha Singh、Prashant Prajapati、Prem P. Yadav

  DOI：10.1039/c5ra20954d

  日期：——

  A transition-metal-free regioselective α-arylation of coumarins and 2-pyridones has been accomplished by the reaction of phenylhydrazines with coumarins or 2-pyridones.

  一种无过渡金属的选择性α-芳基化反应已经成功实现，通过苯基肼与香豆素或2-吡啶酮的反应。
• Heterocyclic antiviral compounds
  申请人：Brameld Kenneth Albert

  公开号：US20100021423A1

  公开（公告）日：2010-01-28

  Compounds having the formula I wherein R 1 , R 2 , R 3 , R 4a , R 4b , R 4c , R 5 , R 6 , R 9 and n are as defined herein are Hepatitis C virus NS5b polymerase inhibitors. Also disclosed are compositions and methods for treating an HCV infection and inhibiting HCV replication.

  具有以下化学式I的化合物，在该式中R1、R2、R3、R4a、R4b、R4c、R5、R6、R9和n的定义如本文所述，是丙型肝炎病毒NS5b聚合酶抑制剂。还公开了用于治疗HCV感染和抑制HCV复制的组合物和方法。
• Iron-Catalyzed Regioselective Direct Arylation at the C-3 Position of <i>N</i>-Alkyl-2-pyridone
  作者：Atanu Modak、Sujoy Rana、Debabrata Maiti

  DOI：10.1021/jo502362k

  日期：2015.1.2

  A number of pharmaceutical compounds possess an arylated 2-pyridone moiety. The existing reports using expensive starting materials and/or superstoichiometric metal salts have prompted us to explore a possible user-friendly method for their synthesis. In this report, we demonstrate an easy-to-handle reaction condition with an iron catalyst for the exclusive generation of C-3-arylated pyridone via C–H

  许多药物化合物具有芳基化的2-吡啶酮部分。使用昂贵的起始原料和/或超化学计量金属盐的现有报道促使我们探索一种可能的用户友好的合成方法。在本报告中，我们证明了使用铁催化剂通过C–H官能化独家生成C-3-芳基吡啶酮的反应条件易于处理。
• Direct and Regioselective Monofluorination of <i>N</i>-Protected Pyridone Derivatives using <i>N</i>-Fluorobenzenesulfonimide (NFSI)
  作者：Fumie Sakurai、Takafumi Yukawa、Takahiko Taniguchi

  DOI：10.1021/acs.orglett.9b02482

  日期：2019.9.20

  pyridone derivatives has been developed using a stable electrophilic fluorinating reagent, N-fluorobenzenesulfonimide (NFSI). Interestingly, the fluorine atom is regioselectively introduced at the position opposite the carbonyl group in the pyridone substrate during the reaction. This method is applicable to a wide range of substrates and allows the regioselective late-stage monofluorination of pyridone

  已使用稳定的亲电氟化试剂N-氟苯磺酰亚胺（NFSI）开发了N-保护的吡啶酮衍生物的直接单氟化。有趣的是，在反应过程中，氟原子在与吡啶酮底物中的羰基相反的位置上区域选择性地引入。该方法适用于广泛的底物，并允许吡啶酮支架的区域选择性晚期单氟化。