2-(4-甲氧基苯基)-1-(3-吡啶基)-乙酮 | 23827-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(4-甲氧基苯基)-1-(3-吡啶基)-乙酮
• 英文名称: 2-(4-methoxyphenyl)-1-(pyridin-3-yl)ethanone
• 英文别名: 2-(4-methoxyphenyl)-1-(3-pyridyl)-1-one；2-(4-methoxy-phenyl)-1-pyridin-3-yl-ethanone；p-methoxybenzyl-(pyridin-3-yl)-ketone；p-methoxybenzyl-(3-pyridyl)-ketone；2-(4-Methoxyphenyl)-1-(3-pyridinyl)-ethanone；2-(4-methoxyphenyl)-1-pyridin-3-ylethanone
• CAS: 23827-45-4
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: RLFQYYQWEAFLSU-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C
• 沸点：
  391.9±22.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基苯基)-1-(3-吡啶基)-乙酮 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 5-(4-Methoxyphenyl)-1-methyl-3-(4-methyl-1,3-thiazol-2-yl)-6-pyridin-3-ylpyridin-2-one
  参考文献：
  名称：

  3-Heteroaryl-2-pyridones:  Benzodiazepine Site Ligands with Functional Selectivity for α2/α3-Subtypes of Human GABA_A Receptor-Ion Channels

  摘要：

  A novel series of 3-heteroaryl-5,6-bis(aryl)-1-methyl-2-pyridones were developed with high affinity for the benzodiazepine (BZ) binding site of human gamma-aminobutyric acid (GABA(A)) receptor ion channels, low binding selectivity for alpha2- and/or alpha3- over alpha1-containing GABA(A) receptor subtypes and high binding selectivity over alpha5 subtypes. High affinity appeared to be associated with a coplanar conformation of the pyridone and sulfur-containing 3-heteroaryl rings resulting from an attractive S...O intramolecular interaction. Functional selectivity (i.e., selective efficacy) for alpha2 and/or alpha3 GABA(A) receptor subtypes over alpha1 was observed in several of these compounds in electrophysiological assays. Furthermore, an alpha3 subtype selective inverse agonist was proconvulsant and anxiogenic in rodents while an alpha2/alpha3 subtype selective partial agonist was anticonvulsant and anxiolytic, supporting the hypothesis that subtype selective BZ site agonists may provide new anxiolytic therapies.

  DOI：

  10.1021/jm0110789
• 作为产物：
  描述：

  2-(吡啶-3-基)-2-(三甲基硅氧基)乙腈 在 硫酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 36.5h， 生成 2-(4-甲氧基苯基)-1-(3-吡啶基)-乙酮
  参考文献：
  名称：

  3-Heteroaryl-2-pyridones:  Benzodiazepine Site Ligands with Functional Selectivity for α2/α3-Subtypes of Human GABA_A Receptor-Ion Channels

  摘要：

  A novel series of 3-heteroaryl-5,6-bis(aryl)-1-methyl-2-pyridones were developed with high affinity for the benzodiazepine (BZ) binding site of human gamma-aminobutyric acid (GABA(A)) receptor ion channels, low binding selectivity for alpha2- and/or alpha3- over alpha1-containing GABA(A) receptor subtypes and high binding selectivity over alpha5 subtypes. High affinity appeared to be associated with a coplanar conformation of the pyridone and sulfur-containing 3-heteroaryl rings resulting from an attractive S...O intramolecular interaction. Functional selectivity (i.e., selective efficacy) for alpha2 and/or alpha3 GABA(A) receptor subtypes over alpha1 was observed in several of these compounds in electrophysiological assays. Furthermore, an alpha3 subtype selective inverse agonist was proconvulsant and anxiogenic in rodents while an alpha2/alpha3 subtype selective partial agonist was anticonvulsant and anxiolytic, supporting the hypothesis that subtype selective BZ site agonists may provide new anxiolytic therapies.

  DOI：

  10.1021/jm0110789

文献信息

• [EN] NOVEL PRECATALYST SCAFFOLDS FOR CROSS-COUPLING REACTIONS, AND METHODS OF MAKING AND USING SAME<br/>[FR] NOUVEAUX SUPPORTS DE PRÉ-CATALYSEURS POUR RÉACTIONS À COUPLAGE MUTUEL, ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：UNIV YALE

  公开号：WO2016057600A1

  公开（公告）日：2016-04-14

  The present invention provides novel transition-metal precatalysts that are useful in preparing active coupling catalysts. In certain embodiments, the precatalysts of the invention are air-stable and moisture-stable. The present invention further provides methods of making and using the precatalysts of the invention.

  本发明提供了新型过渡金属前催化剂，可用于制备活性偶联催化剂。在某些实施例中，本发明的前催化剂具有空气稳定性和湿度稳定性。本发明还提供了制备和使用本发明的前催化剂的方法。
• An improved and practical procedure for the synthesis of substituted phenylacetylpyridines
  作者：Michel Journet、Dongwei Cai、Robert D. Larsen、Paul J. Reider

  DOI：10.1016/s0040-4039(98)00140-3

  日期：1998.3

  A general procedure for the synthesis of substituted phenylacetylpyridines in excellent yields is described using a Horner-Emmons condensation between α-aminoalkylphosphonates of pyridinecarboxaldehydes and benzaldehydes with cesium carbonate at room temperature.

  在室温下使用吡啶甲醛和苯甲醛的α-氨基烷基膦酸酯与碳酸铯之间的霍纳-埃蒙斯缩合，描述了以优异的产率合成取代的苯基乙酰基吡啶的一般方法。
• Selective Monoarylation of Acetate Esters and Aryl Methyl Ketones Using Aryl Chlorides
  作者：Mark R. Biscoe、Stephen L. Buchwald

  DOI：10.1021/ol900295u

  日期：2009.4.16

  Simple, efficient procedures for the monoarylation of acetate esters and aryl methyl ketones using aryl chlorides are presented. Previously, no general method was available to ensure the highly selective monoarylation of these classes of substrates using aryl chlorides. Using palladium precatalysts recently reported by our group, these reactions are easily accomplished under mild conditions that tolerate

  介绍了使用芳基氯对乙酸酯和芳基甲基酮进行单芳基化的简单、有效的程序。以前，没有可用的通用方法来确保使用芳基氯对这些类型的底物进行高选择性单芳基化。使用我们小组最近报道的钯预催化剂，这些反应可以在耐受各种杂环底物的温和条件下轻松完成。
• Imidazole derivatives in the treatment of pain
  申请人：Ciba-Geigy Corporation

  公开号：US03940486A1

  公开（公告）日：1976-02-24

  Compounds of the formula ##SPC1## Wherein R.sub.1 represents lower alkyl, cycloalkyl or phenyl which is optionally substituted by halogen, lower alkyl or lower alkoxy, and one of the groups R.sub.2 and R.sub.3 represents phenyl which is optionally substituted by halogen, lower alkyl, hydroxy, lower alkoxy, lower alkylthio or lower alkylsulphonyl, and the other represents a 6-membered heteroaromatic radical containing 1 or 2 ring nitrogen atoms, their N-oxides and salts, with anti-inflammatory, antinociceptive and antipyretic activity, they are active ingredients of pharmaceutical compositions and can be used for the relief and removal of pain as well as for the treatment of rheumatic, arthritic and other inflammatory complaints; an illustrative example is 2-isopropyl-4(5)-(p-methoxyphenyl)-5(4)-3-pyridyl-imidazole.

  化合物的公式为##SPC1##，其中R.sub.1代表可选择取代卤素、低烷基或低烷氧基的环烷基或苯基；R.sub.2和R.sub.3中的一个代表可选择取代卤素、低烷基、羟基、低烷氧基、低烷硫基或低烷基磺酰基的苯基，另一个代表含有1或2个环氮原子的6元杂环芳基基团。它们的N-氧化物和盐具有抗炎、镇痛和退热活性，是药物组合物的有效成分，可以用于缓解和消除疼痛，以及治疗风湿性、关节性和其他炎症疾病；一个例子是2-异丙基-4（5）-（对甲氧基苯基）-5（4）-3-吡啶基咪唑。
• Precatalyst scaffolds for cross-coupling reactions, and methods of making and using same
  申请人：YALE UNIVERSITY

  公开号：US10894802B2

  公开（公告）日：2021-01-19

  The present invention provides novel transition-metal precatalysts that are useful in preparing active coupling catalysts. In certain embodiments, the precatalysts of the invention are air-stable and moisture-stable. The present invention further provides methods of making and using the precatalysts of the invention.

  本发明提供了可用于制备活性偶联催化剂的新型过渡金属前催化剂。在某些实施方案中，本发明的前催化剂具有空气稳定性和湿度稳定性。本发明进一步提供了制造和使用本发明前催化剂的方法。