3-methyl-4,6-diphenylpyridin-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: 3-methyl-4,6-diphenylpyridin-2(1H)-one
• 英文别名: 3-methyl-4,6-diphenyl-1H-pyridin-2-one
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: WYEOPPXORWZFCS-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

• 作为产物：
  描述：

  (Z)-N-(3-oxo-1,3-diphenylprop-1-enyl)propionamide 在 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 72.0h， 以93%的产率得到3-methyl-4,6-diphenylpyridin-2(1H)-one
  参考文献：
  名称：

  三甲基甲硅烷基三氟甲磺酸盐促进的β-酮烯酰胺的环缩合反应，以及随后的非硝化反应，生成壬基磺酸吡啶-2-基和吡啶-4-基壬酸酯，作为多取代吡啶的柔性前体

  摘要：

  献给恩斯特·绍曼（Ernst Schaumann）教授70岁生日之际 抽象 研究了使用KO t -Bu或三甲基甲硅烷基三氟甲磺酸盐/Hünig碱将β-酮烯酰胺分子内缩合为2-和/或4-吡啶酮衍生物。随后环化产物不被烧蚀，可以通过Suzuki-Miyaura偶联剂轻松纯化并进一步官能化，从而产生新的高度取代的吡啶衍生物。讨论了环缩合的区域选择性对β-酮烯酰胺结构的依赖性。 研究了使用KO t -Bu或三甲基甲硅烷基三氟甲磺酸盐/Hünig碱将β-酮烯酰胺分子内缩合为2-和/或4-吡啶酮衍生物。随后环化产物不被烧蚀，可以通过Suzuki-Miyaura偶联剂轻松纯化并进一步官能化，从而产生新的高度取代的吡啶衍生物。讨论了环缩合的区域选择性对β-酮烯酰胺结构的依赖性。

  DOI：

  10.1055/s-0033-1338548

文献信息

• 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...
• <scp>Base‐Promoted</scp> Synthesis of <scp>3‐Alkenyl</scp> ‐2‐pyridones from <scp> <i>N</i> ‐Propargyl </scp> ‐β‐enaminones and Aryl Aldehydes
  作者：Qingyu Tian、Shangyun Xiao、Guolin Cheng

  DOI：10.1002/cjoc.202100331

  日期：2021.10

  In this article, we report a base-promoted sequential cyclization/aldol-type condensation/isomerization cascade reaction of N-propargyl-β-enaminones with aryl aldehydes. The key step in this protocol is the generation of 1,4-oxazepine anions from N-propargyl-β-enaminones under basic conditions, which are captured by aryl aldehydes. The method allows the formation of one pyridone core and one C—C double

  在本文中，我们报告了N-炔丙基-β-烯胺酮与芳醛的碱促进顺序环化/羟醛型缩合/异构化级联反应。该协议的关键步骤是在碱性条件下从N-炔丙基-β-烯胺酮生成 1,4-氧氮杂阴离子，这些阴离子被芳醛捕获。该方法允许在“一锅”中形成一个吡啶酮核和一个CC双键，并以中等至良好的收率制备多种具有广泛官能团耐受性的致密修饰的吡啶酮衍生物。
• 2-Pyridones from Cyanoacetamides and Enecarbonyl Compounds:  Application to the Synthesis of Nothapodytine B
  作者：Lionel Carles、Kesavaram Narkunan、Sébastien Penlou、Laurence Rousset、Denis Bouchu、Marco A. Ciufolini

  DOI：10.1021/jo025546d

  日期：2002.6.1

  The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-eyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence Of O-2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkyleyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).
• 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.
• Trimethylsilyl Trifluoromethanesulfonate-Promoted Cyclocondensation of β-Ketoenamides and Subsequent Nonaflation to Pyrid-2-yl and Pyrid-4-yl Nonaflates as Flexible Precursors for Polysubstituted Pyridines
  作者：Hans-Ulrich Reissig、Paul Hommes、Sarah Berlin

  DOI：10.1055/s-0033-1338548

  日期：——

  Dedicated to Professor Ernst Schaumann on the occasion of his 70th birthday Abstract The intramolecular condensation of β-ketoenamides to 2- and/or 4-pyridone derivatives using either KOt-Bu or trimethylsilyl trifluoromethanesulfonate/Hünig’s base was investigated. Subsequent nonaflation of the cyclization products allowed a facile purification and further functionalization through Suzuki–Miyaura couplings

  献给恩斯特·绍曼（Ernst Schaumann）教授70岁生日之际 抽象 研究了使用KO t -Bu或三甲基甲硅烷基三氟甲磺酸盐/Hünig碱将β-酮烯酰胺分子内缩合为2-和/或4-吡啶酮衍生物。随后环化产物不被烧蚀，可以通过Suzuki-Miyaura偶联剂轻松纯化并进一步官能化，从而产生新的高度取代的吡啶衍生物。讨论了环缩合的区域选择性对β-酮烯酰胺结构的依赖性。 研究了使用KO t -Bu或三甲基甲硅烷基三氟甲磺酸盐/Hünig碱将β-酮烯酰胺分子内缩合为2-和/或4-吡啶酮衍生物。随后环化产物不被烧蚀，可以通过Suzuki-Miyaura偶联剂轻松纯化并进一步官能化，从而产生新的高度取代的吡啶衍生物。讨论了环缩合的区域选择性对β-酮烯酰胺结构的依赖性。