5-(4-甲氧基苯基)吡啶-2(1h)-酮 | 53242-51-6

• 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
• 中文名称: 5-(4-甲氧基苯基)吡啶-2(1h)-酮
• 英文名称: 5-(4-methoxyphenyl)pyridin-2(1H)-one
• 英文别名: 5-(4-Methoxyphenyl)-2(1H)-pyridinone；5-(4-methoxyphenyl)-1H-pyridin-2-one
• CAS: 53242-51-6
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: CHDTWSPLGKBXPY-UHFFFAOYSA-N

物化性质

• 熔点：
  191 °C (decomp)
• 沸点：
  426.2±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-(4-甲氧基苯基)吡啶-2(1h)-酮 在 palladium on activated charcoal 氢氧化钾 、 氢溴酸 、 氢气 、 lithium hydride 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、4.0 MPa 条件下， 反应 35.0h， 生成 N,N-diisopropyl-2-(4-(1-methyl-6-oxopiperidin-3-yl)phenoxy)acetamide
  参考文献：
  名称：

  Evaluation of 4′-substituted bicyclic pyridones as non-steroidal inhibitors of steroid 5α-reductase

  摘要：

  4'-Substituted bicyclic pyridones were prepared and evaluated as non-steroidal inhibitors of type I and 2 steroid 5 alpha-reductase (SR). A range of 4'-substituents were incorporated into the bicyclic scaffold to investigate SAR within and across different classes of non-steroidal inhibitors of SR. Bicyclic pyridones containing a 4'-benzoyl or long carbon chain tether showed more potent inhibition against type I SR than inhibitors with N-substituted acetamide groups in the 4'-position. SAR derived from 4'-substituted bicyclic pyridones reported here do not correlate with SAR derived from known potent 4'-substituted biaryl acid SR inhibitors. A 4'-benzoyl group is favoured by the active site in both isozymes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.049
• 作为产物：
  描述：

  2-氟-5-溴吡啶 在 四(三苯基膦)钯 盐酸 、 氢氧化钾 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 43.0h， 生成 5-(4-甲氧基苯基)吡啶-2(1h)-酮
  参考文献：
  名称：

  Evaluation of 4′-substituted bicyclic pyridones as non-steroidal inhibitors of steroid 5α-reductase

  摘要：

  4'-Substituted bicyclic pyridones were prepared and evaluated as non-steroidal inhibitors of type I and 2 steroid 5 alpha-reductase (SR). A range of 4'-substituents were incorporated into the bicyclic scaffold to investigate SAR within and across different classes of non-steroidal inhibitors of SR. Bicyclic pyridones containing a 4'-benzoyl or long carbon chain tether showed more potent inhibition against type I SR than inhibitors with N-substituted acetamide groups in the 4'-position. SAR derived from 4'-substituted bicyclic pyridones reported here do not correlate with SAR derived from known potent 4'-substituted biaryl acid SR inhibitors. A 4'-benzoyl group is favoured by the active site in both isozymes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.049
• 作为试剂：
  描述：

  2-羟基-5-溴吡啶 、 4-甲氧基苯硼酸 在 5-(4-甲氧基苯基)吡啶-2(1h)-酮 、 crude product 、 silica gel 、 SiO2 作用下， 以 cyclohexane, ethyl acetate 为溶剂， 反应 4.5h， 生成 5-(4-甲氧基苯基)吡啶-2(1h)-酮
  参考文献：
  名称：

  NOVEL PYRIDINONE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2-RECEPTORS

  摘要：

  本发明涉及新型化合物，特别是按照公式（I）X R1 N Y（I）R2 R3定义的新型吡啶酮衍生物。该发明的化合物是代谢型受体亚型2（“mGluR2”）的正向变构调节剂，适用于治疗或预防与谷氨酸功能障碍相关的神经系统和精神障碍以及涉及代谢型受体亚型2的疾病。特别是，这些疾病是选择自焦虑、精神分裂症、偏头痛、抑郁症和癫痫等中枢神经系统疾病的一组。本发明还涉及制备这种化合物和组合物的制药组合物和制备过程，以及利用这种化合物预防和治疗涉及mGluR2的这些疾病的用途。

  公开号：

  US20070213323A1

文献信息

• [EN] NOVEL PYRIDINONE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2-RECEPTORS<br/>[FR] NOUVEAUX DERIVES DE PYRIDINONE ET LEUR UTILISATION EN TANT QUE MODULATEURS ALLOSTERIQUES POSITIFS DES RECEPTEURS MGLUR2
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006030032A1

  公开（公告）日：2006-03-23

  The present invention relates to novel compounds, in particular novel pyridinone derivat ives according to Formula (I) X R1 N Y (I) R2 R3 wherein all radicals are defined in the application. The compounds according to the invention are positive allosteric modulators of metabotropic receptors - subt ype 2 ('mGluR2') which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. In particular, such diseases are central nervous system disorders selected from the group of anxiety, schizophrenia, migraine, depression, and epilepsy. The invention is also directed to pharmaceutical compositions and processes to prepare such compounds and compositions, as well as to the use of such compounds for the prevention and treatment of such diseases in which mGluR2 is involved.

  本发明涉及新化合物，特别是根据式（I）X R1 N Y（I）R2 R3定义的新吡啶酮衍生物。根据本发明的化合物是代谢型受体-亚型2（'mGluR2'）的阳性变构调节剂，对于治疗或预防与谷氨酸功能障碍相关的神经和精神障碍以及涉及代谢型受体的mGluR2亚型的疾病具有用处。特别是，这些疾病是从焦虑、精神分裂症、偏头痛、抑郁症和癫痫等中枢神经系统障碍组中选择的。该发明还涉及制备此类化合物和组合物的药物组合物和过程，以及利用这类化合物预防和治疗涉及mGluR2的这类疾病。
• COMPOUNDS AND METHODS FOR TREATING INFLAMMATORY AND FIBROTIC DISORDERS
  申请人：Kossen Karl

  公开号：US20090318455A1

  公开（公告）日：2009-12-24

  Disclosed are compounds and methods for treating inflammatory and fibrotic disorders, including methods of modulating a stress activated protein kinase (SAPK) system with an active compound, wherein the active compound exhibits low potency for inhibition of the p38 MAPK; and wherein the contacting is conducted at a SAPK-modulating concentration that is at a low percentage inhibitory concentration for inhibition of the p38 MAPK by the compound. Also disclosed are derivatives and analogs of pirfenidone, useful for modulating a stress activated protein kinase (SAPK) system.

  公开了用于治疗炎症和纤维化疾病的化合物和方法，包括用活性化合物调节应激活化蛋白激酶（SAPK）系统的方法，其中活性化合物对p38 MAPK的抑制效力较低；并且其中接触是在SAPK调节浓度下进行的，该浓度对化合物抑制p38 MAPK的抑制浓度百分比较低。还公开了吡非尼酮的衍生物和类似物，它们可用于调节应激活化蛋白激酶（SAPK）系统。
• Divergent synthesis of arylated pyridin-2(1H)-one derivatives via metal-catalysed cross-coupling processes
  作者：Jamie S. Siddle、Andrei S. Batsanov、Stuart T. Caldwell、Graeme Cooke、Martin R. Bryce

  DOI：10.1016/j.tet.2010.05.108

  日期：2010.8

  1,5-Di(hetero)arylated-pyridin-2(1H)-one derivatives have been readily obtained in good yields starting from 2-fluoro-5-pyridylboronic acid. The sequence comprises three steps: (i) palladium-catalysed Suzuki-Miyaura reaction; (ii) base-catalysed hydrolysis; (iii) copper-catalysed C–N coupling. X-ray crystal structures are reported for selected pyridin-2(1H)-one derivatives. These compounds are of interest

  从2-氟-5-吡啶基硼酸开始容易地以高收率获得1，5-二（杂）芳基化吡啶-2-2（1 H）-one衍生物。该序列包括三个步骤：（i）钯催化的Suzuki-Miyaura反应；（ii）碱催化水解；（iii）铜催化的C–N耦合。报告了选定的吡啶-2（1 H）-one衍生物的X射线晶体结构。这些化合物作为用于药物发现的新支架是令人感兴趣的。
• Regioselective Synthesis of N-Heteroaromatic Trifluoromethoxy Compounds by Direct O−CF₃ Bond Formation
  作者：Apeng Liang、Shuaijun Han、Zhenwei Liu、Liang Wang、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1002/chem.201505181

  日期：2016.4.4

  the synthesis of ortho‐N‐heteroaromatic trifluoromethoxy derivatives by site‐specific O−CF3 bond formation using hydroxylated N‐heterocycles and Togni's reagent is described. The approach enables the unprecedented syntheses of a wide range of six or five‐membered N‐heteroaromatic trifluoromethoxy compounds containing one or two heteroatoms from most commonly used hydroxylated N‐heterocycles. Notable

  描述了使用羟基化的N-杂环和Togni试剂通过位点特异性O-CF 3键形成来合成邻-N-杂芳族三氟甲氧基衍生物的第一步方法。该方法可以前所未有地合成六到五元的N-杂芳族三氟甲氧基化合物，这些化合物含有一个或两个来自最常用的羟基化N-杂环的杂原子。该方法的显着优势包括其简单，温和的条件，避免了对金属或有毒试剂的需求以及与各种官能团的相容性。此外，该方法特别适合大规模应用。
• Pyridinone derivatives and their use as positive allosteric modulators of mGluR2-receptors
  申请人：Bolea Christelle Martine

  公开号：US08399493B2

  公开（公告）日：2013-03-19

  The present invention relates to methods for treating or controlling schizophrenia in a mammal using compounds having the Formula (I), wherein M1 and M2 are defined in the application.

  本发明涉及使用具有式(I)的化合物治疗或控制哺乳动物的精神分裂症的方法，其中M1和M2在申请中有定义。