1-甲基-4-苯基-2(1H)-吡啶酮 | 67970-80-3

• 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-甲基-4-苯基-2(1H)-吡啶酮
• 英文名称: 1-methyl-4-phenyl-2(1H)-pyridone
• 英文别名: 1-methyl-4-phenyl-2-pyridone；1-methyl-4-phenyl-1H-pyridin-2-one；1-Methyl-4-phenyl-2(1H)-pyridon；2(1H)-Pyridinone, 1-methyl-4-phenyl-；1-methyl-4-phenylpyridin-2-one
• CAS: 67970-80-3
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: OVNWRUULQMZZNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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-甲基-4-苯基-2(1H)-吡啶酮 在 lithium aluminium tetrahydride 、 titanium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到1-甲基-4-苯基-1,2,3,6-四氢吡啶
  参考文献：
  名称：

  Selective Reductions of 1-Methyl-4-phenyl-2-pyridone

  摘要：

  We have explored the reactions of 1-methyl-4-phenyl-2-pyridone (5) with various reducing agents in an effort to develop synthetic approaches to specifically deuterium-labeled 1,4-disubstituted 1,2,3,6-tetrahydropyridine analogs needed for metabolic and enzyme mechanistic studies. Reactions with NaBH4 in CH3OH or THF, LiAl(O-t-Bu)(3)H in THF, and Al(i-Bu)(2)H(DIBALH) in THF resulted in quantitative recovery of starting material. On the other hand, treatment with BH3 in THF unexpectedly led to the formation of 4-phenylpyridine (7) in 98% yield. LiAIH(4) in THF or Et(2)O and Red-Al in THF gave varying amounts of the 3,6-dihydro-2-pyridone 8 and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (1). In the presence of TiCl3, LiAlH4 in THF at 0 degrees C converted 5 to 1 in 97% yield. LiB(s-Bu)(3)H (L-Selectride) in THF gave exclusively the 1,4-reduction product 8. Base catalyzed isomerization of 8 provided the conjugated 5,6-dihydro-2-pyridone 4. The applications of these reactions with deuterated reagents provide insights into the reaction pathways and several avenues for the regioselective synthesis of the required deuterium-labeled compounds.

  DOI：

  10.1021/jo951529v
• 作为产物：
  描述：

  2-氯-4-溴吡啶 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-甲基-4-苯基-2(1H)-吡啶酮
  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

• Reactions of 1-unsubstituted tautomeric 2-pyridones with benzyne.
  作者：MASAYUKI KUZUYA、AKIHIRO NOGUCHI、SHOJI KAMIYA、TAKACHIYO OKUDA

  DOI：10.1248/cpb.33.2313

  日期：——

  The reactions of 1-unsubstituted 2-pyridones with benzyne afforded the Diels-Alder adduct, 5, 6-benzo-2-azabarrelen-3 (2H)-ones, together with a large amount of the Michael-type adduct, 2-phenoxypyridines.

  1-未取代的2-吡啶酮与苯炔的反应生成了Diels-Alder加成产物5, 6-苯并-2-氮杂巴雷ланы-3 (2H)-酮，同时生成了大量的迈克尔型加成产物2-苯氧基吡啶。
• Direct C–H Sulfonylimination of Pyridinium Salts
  作者：Lihua Luo、Juan Tang、Rui Sun、Wenjing Li、Xueli Zheng、Maoling Yuan、Ruixiang Li、Hua Chen、Haiyan Fu

  DOI：10.1021/acs.orglett.2c00725

  日期：2022.4.22

  A direct pyridinium C–H sulfonylimination has been developed for the synthesis of sulfonyl iminopyridine derivatives with high efficiency. This transformation features the direct and efficient formation of a C═N bond with a high functional group tolerance under metal-free conditions. The spectroscopic properties potentially enable these sulfonyl iminopyridine compounds to be useful new emitting materials

  已经开发了直接吡啶鎓 C-H 磺酰亚胺化，用于高效合成磺酰基亚氨基吡啶衍生物。这种转变的特点是在无金属条件下直接有效地形成具有高官能团耐受性的 C=N 键。光谱特性可能使这些磺酰基亚氨基吡啶化合物成为有用的新型发光材料。
• Ultra‐long Near‐infrared Repeatable Photochemical Afterglow Mediated by Reversible Storage of Singlet Oxygen for Information Encryption
  作者：Lei Chen、Kuangshi Sun、Donghao Hu、Xianlong Su、Linna Guo、Jiamiao Yin、Yuetian Pei、Yiwei Fan、Qian Liu、Ming Xu、Wei Feng、Fuyou Li

  DOI：10.1002/anie.202218670

  日期：2023.3.20

  general strategy to realize repeatable photochemical afterglow (RPA) based on the reversible storage of singlet oxygen. Ultra-long near-infrared afterglow was achieved via the singlet oxygen-sensitized fluorescence approach, and its intensity shows no significant reduction over 50 excitation cycles. The RPA system was further applied for attacker-misleading information encryption, presenting a repeatable

  我们展示了一种基于单线态氧可逆存储实现可重复光化学余辉 (RPA) 的一般策略。通过单线态氧敏荧光方法实现了超长近红外余辉，其强度在 50 个激发循环后没有显着降低。RPA 系统进一步应用于攻击者误导信息加密，呈现可重复读出。
• Design of 2‐Pyridone Fluorophores for Brighter Emissions at Longer Wavelengths
  作者：Dong Sun Kim、Younghun Kim、Dongwhan Lee、Yan Lee

  DOI：10.1002/chem.202303458

  日期：2024.3.12

  sentence: A rational design strategy for 2-pyridone-based fluorophores with bright emission at long wavelengths is proposed. An intramolecular charge transfer-based 2-pyridone fluorophore with large molar absorptivity (ϵ=20,100 M−1 cm−1), longer emission wavelength (λem=539 nm), high emission quantum yield (ϕF=74 %), and large Stokes shift (Δv=5720 cm−1) is developed by the strategy.

  TOC 句子：提出了一种在长波长下具有明亮发射的基于 2-吡啶酮的荧光团的合理设计策略。基于分子内电荷转移的2-吡啶酮荧光团，具有大摩尔吸收率（ϵ=20,100 M −1 cm −1 ）、更长的发射波长（λ em =539 nm）、高发射量子产率（Φ F =74 %），以及该策略产生了大的斯托克斯位移（Δv=5720 cm -1 ）。
• Gisby, Graham P.; Royall, Sven E.; Sammes, Peter G., Journal of the Chemical Society. Perkin transactions I, 1982, p. 169 - 174
  作者：Gisby, Graham P.、Royall, Sven E.、Sammes, Peter G.

  DOI：——

  日期：——