4-氯-1-甲基吡啶-2(1H)-酮 | 53937-04-5

• 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: 4-氯-1-甲基吡啶-2(1H)-酮
• 英文名称: 4-chloro-1-methyl-2-pyridone
• 英文别名: N-Methyl-4-chlor-pyridon-(2)；4-Chlor-1-methyl-2(1H)-pyridon；4-chloro-1-methyl-1H-pyridin-2-one；4-Chloro-1-methylpyridin-2(1H)-one；4-chloro-1-methylpyridin-2-one
• CAS: 53937-04-5
• 化学式: C₆H₆ClNO
• 分子量: 143.573
• InChiKey: GCKKXNHKKLVUMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  4-氯-1-甲基吡啶-2(1H)-酮 、 tert-butyl (6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)carbamate 在 Pd-118 作用下， 以 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Discovery of potent, selective small molecule inhibitors of α-subtype of type III phosphatidylinositol-4-kinase (PI4KIIIα)

  摘要：

  The discovery and optimisation of novel, potent and selective small molecule inhibitors of the alpha-isoform of type III phosphatidylinositol-4-kinase (PI4K alpha) are described. Lead compounds show cellular activity consistent with their PI4K alpha potency inhibiting the accumulation of IP1 after PDGF stimulation and reducing cellular PIP, PIP2 and PIP3 levels. Hence, these compounds are useful in vitro tools to delineate the complex biological pathways involved in signalling through PI4Ka. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.093
• 作为产物：
  描述：

  4-氯-2-羟基吡啶 、 碘甲烷 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 苯 为溶剂， 反应 24.0h， 以92%的产率得到4-氯-1-甲基吡啶-2(1H)-酮
  参考文献：
  名称：

  Direct Arylation of 2-Pyridones; Photostimulated SRN1 Reaction between Cesium Phenoxides and Chloro-2-pyridones

  摘要：

  DOI：

  10.3987/com-99-s18

文献信息

• [EN] PYRIMIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS DE PYRIMIDINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：GENENTECH INC

  公开号：WO2010014939A1

  公开（公告）日：2010-02-04

  Disclosed are compounds of Formula I, including steroisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, that are useful in modulating PIKK related kinase signaling, e.g., mTOR, and for the treatment of diseases (e.g., cancer) that are mediated at least in part by the dysregulation of the PIKK signaling pathway (e.g., mTOR).

  揭示了公式I的化合物，包括立体异构体、几何异构体、互变异构体、溶剂合物、代谢物和其药学上可接受的盐，这些化合物在调节PIKK相关激酶信号传导方面很有用，例如mTOR，并用于治疗至少部分由PIKK信号传导途径失调引起的疾病（例如癌症）。
• 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。
• Iridium-Catalyzed Site-Selective C–H Borylation of 2-Pyridones
  作者：Koji Hirano、Masahiro Miura、Wataru Miura

  DOI：10.1055/s-0036-1588735

  日期：2017.11

  An iridium-catalyzed site-selective C–H borylation of 2-pyridones has been developed. The site selectivity is predominantly controlled by steric factors, and we can access C4, C5, and C6 C–H on the 2-pyridone ring by the judicious choice of ligand and solvent. Subsequent Suzuki–Miyaura cross-coupling of the borylated products also proceeds to form the corresponding arylated pyridones in good overall

  开发了一种铱催化的 2-吡啶酮位点选择性 C-H 硼化反应。位点选择性主要由空间因素控制，我们可以通过明智地选择配体和溶剂来访问 2-吡啶酮环上的 C4、C5 和 C6 C-H。随后硼化产物的 Suzuki-Miyaura 交叉偶联也以良好的总收率形成相应的芳基化吡啶酮。
• Diels-Alder Reaction of 2(1H)-Pyridones Acting as Dienes
  作者：Masato Hoshino、Hisao Matsuzaki、Reiko Fujita

  DOI：10.1248/cpb.56.480

  日期：——

  Diels–Alder reactions between N-phenylmaleimide, acting as the dienophile, and 2(1H)-pyridones having a methoxy or a chloro substituent, were carried out, under atmospheric and high pressure conditions, to give the corresponding isoquinuclidine derivatives. Stereoselectivity of the Diels–Alder reactions was studied using molecular orbital calculations.

  在常压和高压条件下，N-苯基富马酸酐作为二烯亲电体，与具有甲氧基或氯取代基的2(1H)-吡啶酮进行Diels–Alder反应，得到相应的异喹啉衍生物。通过分子轨道计算研究了Diels–Alder反应的立体选择性。
• PYRIMIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  申请人：Bergeron Philippe

  公开号：US20100069357A1

  公开（公告）日：2010-03-18

  Disclosed are compounds of Formula I, including steroisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, that are useful in modulating PIKK related kinase signaling, e.g., mTOR, and for the treatment of diseases (e.g., cancer) that are mediated at least in part by the dysregulation of the PIKK signaling pathway (e.g., mTOR).

  本发明涉及I式化合物，包括其立体异构体、几何异构体、互变异构体、溶剂化物、代谢物和药学上可接受的盐，其对调节PIKK相关激酶信号传导，例如mTOR，并用于治疗至少部分由PIKK信号通路失调介导的疾病（例如癌症）具有用处。