3-benzoyl-2,4-dimethylpyridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-2,4-dimethylpyridine
• 英文别名: (2,4-dimethylpyridin-3-yl)(phenyl)methanone；(2,4-Dimethylpyridin-3-yl)-phenylmethanone；(2,4-dimethylpyridin-3-yl)-phenylmethanone
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: GZXOHLYJVHJNPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯-4-溴吡啶 在 四甲基乙二胺 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 、 copper(l) chloride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 3-benzoyl-2,4-dimethylpyridine
  参考文献：
  名称：

  钯催化自动串联法从二卤代二芳基酮合成取代的氮杂芴酮†

  摘要：

  通过将Suzuki或Heck偶合与直接环化芳基化反应相结合，在钯催化下，由不同的二卤代二芳基酮合成了取代的氮杂芴酮。确定条件以使自动串联过程能够成功地由3-（溴苯甲酰基）-或3-苯甲酰基-4-溴-2-氯吡啶以及4-苯甲酰基-2,3-和4-苯甲酰基-2成功进行，5-二氯吡啶。

  DOI：

  10.1039/c4ob01629g

文献信息

• Synthesis of 3‐Keto Pyridines from the Conjugated Allenone – Alkynylamine Oxidative Cyclization Catalyzed by Supported Au Nanoparticles
  作者：Michael Fragkiadakis、Marios Kidonakis、Leandros Zorba、Manolis Stratakis

  DOI：10.1002/adsc.201901451

  日期：2020.2.21

  to substituted 3‐keto pyridines or 4‐picolines in very good yields. This pathway is in contrast to their known cyclization in the presence of Au(I) or Au(III) catalysts which provides 1,4‐oxazepines, instead. The enaminones are formed in situ upon mixing a conjugated allenone or allenyl ester with the alkynylamine, thus the pyridine‐forming transformation is typically a one pot process.

  TiO 2上的可回收负载型Au纳米颗粒催化N-炔丙基或N-同炔丙基β-烯胺酮的环化，然后进行脱氢（芳构化），从而以非常好的收率产生取代的3-酮吡啶或4-甲基吡啶。该途径与已知在Au（I）或Au（III）催化剂存在下环化的相反，后者提供1,4-氧杂氮杂pine。烯胺酮是在将共轭的Allenone或Allenyl酯与炔基胺混合后原位形成的，因此形成吡啶的转化通常是一锅法。
• Substituted azafluorenones: access from dihalogeno diaryl ketones by palladium-catalyzed auto-tandem processes and evaluation of their antibacterial, antifungal, antimalarial and antiproliferative activities
  作者：Nada Marquise、Floris Chevallier、Ekhlas Nassar、Michel Frédérich、Allison Ledoux、Yury S. Halauko、Oleg A. Ivashkevich、Vadim E. Matulis、Thierry Roisnel、Vincent Dorcet、Florence Mongin

  DOI：10.1016/j.tet.2015.12.050

  日期：2016.2

  Substituted azafluorenones were synthesized from dihalogeno diaryl ketones under palladium catalysis by combining, in auto -tandem processes, Suzuki coupling and intramolecular arylation reactions. Different dihalogenated diaryl ketones, prepared by sequential deprotocupration-aroylation, were identified as suitable substrates to this purpose. Conditions were identified to allow successful syntheses of several 6-/7-arylated 4-azafluorenones, 1 -substituted 4-azafluorenones, 2-phenyl-3-azafluorenone, and 4-phenyl-3-azafluorenone from 3-(bromobenzoyl)-2-chloropyridines, 3-benzoyl-4-bromo-2-chloropyridines, 4-benzoyl-2,5-dichloropyridine, and 4-benzoyl-2,3-dichloropyridine, respectively. Some of the synthesized compounds exhibit interesting biological properties. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of substituted azafluorenones from dihalogeno diaryl ketones by palladium-catalyzed auto-tandem processes
  作者：Nada Marquise、Vincent Dorcet、Floris Chevallier、Florence Mongin

  DOI：10.1039/c4ob01629g

  日期：——

  Substituted azafluorenones were synthesized from different dihalogeno diaryl ketones under palladium catalysis by combining either Suzuki or Heck coupling with direct cyclizing arylation. Conditions were identified to allow both auto-tandem processes to proceed successfully from 3-(bromobenzoyl)- or 3-benzoyl-4-bromo-2-chloropyridines, as well as 4-benzoyl-2,3- and 4-benzoyl-2,5-dichloropyridines.

  通过将Suzuki或Heck偶合与直接环化芳基化反应相结合，在钯催化下，由不同的二卤代二芳基酮合成了取代的氮杂芴酮。确定条件以使自动串联过程能够成功地由3-（溴苯甲酰基）-或3-苯甲酰基-4-溴-2-氯吡啶以及4-苯甲酰基-2,3-和4-苯甲酰基-2成功进行，5-二氯吡啶。