1-吡啶-2-基吡啶-2-酮 | 3480-65-7

• 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
• 中文名称: 1-吡啶-2-基吡啶-2-酮
• 英文名称: [1,2']bipyridinyl-2-one
• 英文别名: 2H-[1,2'-bipyridin]-2-one；1-(2-pyridyl)-2-pyridone；2H-[1,2′-bipyridin]-2-one；N-(Pyridyl-2)-pyridon-(2)；1-(2'-Pyridyl)-2-pyridon；[1(2H),2'-Bipyridin]-2-one；1-pyridin-2-ylpyridin-2-one
• CAS: 3480-65-7
• 化学式: C₁₀H₈N₂O
• mdl: MFCD00234620
• 分子量: 172.186
• InChiKey: TTYWSMWHPYKDEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-吡啶-2-基吡啶-2-酮 在 氯 、 溶剂黄146 作用下， 生成 5-chloro-2H-[1,2'-bipyridin]-2-one
  参考文献：
  名称：

  de Villiers; den Hertog, Recueil des Travaux Chimiques des Pays-Bas, 1956, vol. 75, p. 1303,1307

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘吡啶 在 copper(l) iodide 、 potassium carbonate 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以44%的产率得到1-吡啶-2-基吡啶-2-酮
  参考文献：
  名称：

  An improved Ullmann–Ukita–Buchwald–Li conditions for CuI-catalyzed coupling reaction of 2-pyridones with aryl halides

  摘要：

  An effective CuI-trans-N,N'-dimethylcyclohexane-1,2-diamine (DMCDA)-K2CO3-cataIyzed coupling reaction of 2-pyridones with aryl halides is described. Under our conditions, DMCDA was found to be an effective catalyst that facilitates the coupling reactions even in toluene, a common industrial solvent. In addition, 3-bromopyridine could also be coupled effectively under these conditions, indicating that the catalytic reactivity of this system is high. The reaction could be applied for polymer modification and iterative oligo-pyridone synthesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.063

文献信息

• Synthesis of Unsymmetrically Substituted Bipyridines by Palladium-Catalyzed Direct C−H Arylation of Pyridine <i>N</i>-Oxides
  作者：Sasa Duric、C. Christoph Tzschucke

  DOI：10.1021/ol200565u

  日期：2011.5.6

  Substituted bipyridines were efficiently prepared by direct coupling between pyridine N-oxides and halopyridines using a palladium catalyst. Pyridine N-oxides with electron-withdrawing substitutents gave the best yields. This method allows the convenient preparation of 2,2′-, 2,3′-, and 2,4′-bipyridines which are useful as functionalized ligands for metal complexes or as building blocks for supramolecular

  通过使用钯催化剂在吡啶的N-氧化物和卤代吡啶之间直接偶联，可以有效地制备取代的联吡啶。带有吸电子取代基的吡啶N-氧化物的收率最高。该方法允许方便地制备2,2'-，2,3'-和2,4'-联吡啶，其可用作金属配合物的官能化配体或用作超分子结构的结构单元。
• Iridium(III)-Catalyzed Regiocontrolled Direct Amidation of Isoquinolones and Pyridones
  作者：Debapratim Das、Rajarshi Samanta

  DOI：10.1002/adsc.201701244

  日期：2018.1.17

  Iridium(III)‐catalyzed highly regiocontrolled C3/C8 amidation of isoquinolones and C6 amidation of 2‐pyridones has been successfully accomplished with various azides. The optimized method is operationally simple with a broad substrate scope. The protocol has been found to be scalable.

  用各种叠氮化物成功地完成了铱（III）催化的高区域控制的异喹诺酮的C3 / C8酰胺化和2-吡啶酮的C6酰胺化。优化的方法操作简单，具有广泛的基材范围。已经发现该协议是可伸缩的。
• Visible-light-mediated decarboxylative alkylation of 2-pyridone derivatives <i>via</i> a C3-selective C–H functionalization
  作者：Worawat Niwetmarin、Rungroj Saruengkhanphasit、Chatchakorn Eurtivong、Somsak Ruchirawat

  DOI：10.1039/d1ob01829a

  日期：——

  direct C–H functionalization approach to access C3-alkylated 2-pyridone derivatives is reported. This study utilizes N-hydroxyphthalimide (NHPI) esters of various carboxylic acids as sources of alkyl radicals by reductive cleavage under photocatalytic reaction conditions. The carbon–carbon bond formation occurred site-selectively at C3 of 2-pyridone to give the desired products in moderate to good yields

  报道了一种直接的 C-H 官能化方法来获得 C3-烷基化的 2-吡啶酮衍生物。本研究利用各种羧酸的N-羟基邻苯二甲酰亚胺 (NHPI) 酯作为烷基自由基的来源，在光催化反应条件下通过还原裂解。碳-碳键的形成在 2-吡啶酮的 C3 位点选择性地发生，从而以中等至良好的产率得到所需的产物。该方法能够更快地获得可用于合成小分子药物的C3-烷基化吡啶酮化合物。
• Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents
  作者：Erwann Grenet、Ashis Das、Paola Caramenti、Jérôme Waser

  DOI：10.3762/bjoc.14.102

  日期：——

  The C-H indolation of heteroarenes was realized using the benziodoxolone hypervalent iodine reagents indoleBXs. Functionalization of the C-H bond in bipyridinones and quinoline N-oxides catalyzed by a rhodium complex allowed to incorporate indole rings into aza-heteroaromatic compounds. These new transformations displayed complete regioselectivity for the C-6 position of bipyridinones and the C-8 position

  杂芳烃的CH吲哚是使用苯并恶唑酮高价碘试剂吲哚BX来实现的。通过吡啶配合物催化的联吡啶和酮喹啉N-氧化物中的CH键官能化可将吲哚环并入氮杂杂芳族化合物中。这些新的转化显示出对联吡啶的C-6位和喹啉N-氧化物的C-8位具有完全的区域选择性，并具有宽泛的官能度，例如卤素，醚或三氟甲基。
• Rh(I)‐Catalyzed Direct C6−H Arylation of 2‐Pyridones with Aryl Carboxylic Acids
  作者：Haoqiang Zhao、Jianbin Xu、Xin Xu、Yixiao Pan、Zexin Yu、Lijin Xu、Qinghua Fan、Patrick J. Walsh

  DOI：10.1002/adsc.202100596

  日期：2021.8.13

  Rh(I)-catalyzed C6-selective C−H arylation of 2-pyridones with inexpensive, readily available, safe and structurally diverse aryl carboxylic acids with the aid of a pyridine directing group is developed. This decarbonylative arylation protocol features an easy-to-handle catalytic system, and is amenable to diversely substituted 2-pyridones and aryl carboxylic acids. It allows access to a wide range

  开发了在吡啶导向基团的帮助下，Rh(I) 催化的 C6 选择性 C-H 芳基化 2-吡啶酮与廉价、容易获得、安全且结构多样的芳基羧酸。这种脱羰芳基化方案具有易于操作的催化系统，适用于多种取代的 2-吡啶酮和芳基羧酸。它允许使用范围广泛的 C6-芳基化 2-吡啶酮，包括那些使用传统 CH 芳基化工艺难以制备的化合物。该方法可耐受各种电子中性、富电子和缺电子官能团，并以 41-91% 的产率提供产品。

表征谱图