1-o-tolylpyridin-2(1H)-one | 54774-86-6

• 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-o-tolylpyridin-2(1H)-one
• 英文别名: 2(1H)-Pyridinone, 1-(2-methylphenyl)-；1-(2-methylphenyl)pyridin-2-one
• CAS: 54774-86-6
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: QPAWOFDWNBLYCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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

• 作为产物：
  描述：

  2-羟基吡啶 、 tri-o-tolylbismuth(V) chloride 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到1-o-tolylpyridin-2(1H)-one
  参考文献：
  名称：

  在无铜条件下用五价有机铋试剂对吡啶-2(1H)-酮进行 N-芳基化

  摘要：

  使用三芳基或四芳基有机铋 (V) 试剂（如二氯化三芳基铋）通过配体偶联反应建立了一种用于吡啶-2(1H)-酮和相关杂芳族内酰胺的 N-芳基化的有效方法。此外，通过使用烯基三芳基铋 (V) 试剂类似地实现了吡啶-2(1H)-one 的 N-烯基化。

  DOI：

  10.1246/bcsj.79.761

文献信息

• Synthesis of<i>N</i>-Aryl Pyridin-2-ones via Ligand Coupling Reactions Using Pentavalent Organobismuth Reagents
  作者：Kazuhiro Ikegai、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.1496

  日期：2005.11

  An efficient method for the synthesis of N-aryl pyridin-2-ones was established by way of ligand coupling reactions using pentavalent organobismuth reagents such as triarylbismuth dichlorides.

  通过使用五价有机铋试剂（如二氯化三芳基铋）的配体偶联反应，建立了一种合成 N-芳基吡啶-2-酮的有效方法。
• <i>N</i>- and <i>O</i>-arylation of pyridin-2-ones with diaryliodonium salts: base-dependent orthogonal selectivity under metal-free conditions
  作者：Masami Kuriyama、Natsumi Hanazawa、Yusuke Abe、Kotone Katagiri、Shimpei Ono、Kosuke Yamamoto、Osamu Onomura

  DOI：10.1039/d0sc02516j

  日期：——

  N- and O-arylation reactions of pyridin-2-ones as ambident nucleophiles have been achieved with diaryliodonium salts on the basis of base-dependent chemoselectivity. In the presence of N,N-diethylaniline in fluorobenzene, pyridin-2-ones were very selectively converted to N-arylated products in high yields. On the other hand, the O-arylation reactions smoothly proceeded with the use of quinoline in chlorobenzene

  基于对碱的化学选择性，用二芳基碘鎓盐实现了作为环境亲核体的吡啶-2-酮的无金属N-和O-芳基化反应。在氟苯中存在N，N-二乙基苯胺时，吡啶-2-酮非常有选择地以高收率转化为N-芳基化产物。另一方面，通过在氯苯中使用喹啉使O-芳基化反应顺利进行，从而导致高收率和选择性。在这些方法中，除吡啶-4-酮和一组二芳基碘鎓盐之外，还接受了多种吡啶-2-酮和一组二芳基碘鎓盐作为合适的反应伙伴。
• Substituent Effects of 2-Pyridones on Selective O-Arylation with Diaryliodonium Salts: Synthesis of 2-Aryloxypyridines under Transition­-Metal-Free Conditions
  作者：Dong-Liang Mo、Xiao-Hua Li、Ai-Hui Ye、Cui Liang

  DOI：10.1055/s-0036-1591884

  日期：2018.4

  An efficient transition-metal-free strategy to synthesize 2-aryloxypyridine derivatives has been developed by a selective O-arylation of 2-pyridones with diaryliodonium salts. The reaction was compatible with a series of functional groups for 2-pyridones and diaryliodonium salts such as halides, nitro, cyano, and ester groups. The substituents at the C6-position of 2-pyridones favored O-arylation products because of steric hindrance. The reaction was easily performed on a gram-scale and 6-chloro-2-pyridone was a good precursor to access various unsubstituted 2-aryloxypyridines by dehalogenation. A P2Y1 lead compound analogue could be prepared in good yield over two steps.

  开发了一种高效的过渡金属自由策略，通过选择性的氧芳基化2-吡啶酮与二芳基碘盐合成2-芳氧基吡啶衍生物。该反应与一系列功能团对2-吡啶酮和二芳基碘盐兼容，如卤素、硝基、氰基和酯基等。2-吡啶酮的C6位取代基有利于氧芳基化产物的生成，因为存在立体位阻。该反应易于在克级规模上进行，并且6-氯-2-吡啶酮是通过去卤代法获得各种未取代的2-芳氧基吡啶的良好前体。通过两步反应可以以较高产率制备P2Y1前体类似物。
• Cu-Catalyzed <i>N</i>- and <i>O</i>-Arylation of 2-, 3-, and 4-Hydroxypyridines and Hydroxyquinolines
  作者：Ryan A. Altman、Stephen L. Buchwald

  DOI：10.1021/ol062904g

  日期：2007.2.1

  With use of Cu-based catalysts, 2- and 4-hydroxypyridines were N-arylated in modest to excellent yields. In the case of 2-hydroxypyridine, the use of 4,7-dimethoxy-1,10-phenanthroline, 3, expanded the scope of previous literature reports to include the use of N-containing heteroaryl halides, and 2-substituted aryl halides. In addition, by using a copper catalyst based on 2,2,6,6-tetramethylheptane-3,5-dione, 4, the first N-arylations of 4-hydroxypyridines and O-arylations of 3-hydroxypyridines with aryl bromides and iodides have been accomplished.
• Pyridone Directed Ru-Catalyzed Olefination of <i>sp</i>²(C–H) Bond Using Michael Acceptors: Creation of Drug Analogues
  作者：Smruti Ranjan Mohanty、Namrata Prusty、Tanmayee Nanda、Shyam Kumar Banjare、Ponneri C. Ravikumar

  DOI：10.1021/acs.joc.2c00428

  日期：2022.5.6