4(1H)-吡啶酮,2,3-二氢-2-苯基- | 126378-84-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4(1H)-吡啶酮,2,3-二氢-2-苯基-
• 英文名称: 2-phenyl-2,3-dihydropyridin-4(1H)-one
• 英文别名: 4(1H)-Pyridinone, 2,3-dihydro-2-phenyl-；2-phenyl-2,3-dihydro-1H-pyridin-4-one
• CAS: 126378-84-5
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: UHNSISVZKUXMPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4(1H)-吡啶酮,2,3-二氢-2-苯基- 在 sodium periodate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 26.0h， 以93%的产率得到3-amino-3-phenylpropanoic acid hydrochloride
  参考文献：
  名称：

  Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives

  摘要：

  A new method for the synthesis of beta-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NalO(4) and subsequently with base gave the corresponding beta-amino acids in a one-pot procedure. The reactions have been monitored by H-1 NMR indicating that the beta-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.

  DOI：

  10.1021/ol0485518
• 作为产物：
  描述：

  4-甲氧基吡啶 在 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.92h， 生成 4(1H)-吡啶酮,2,3-二氢-2-苯基-
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship Studies of Novel Dihydropyridones as Androgen Receptor Modulators

  摘要：

  A library of 3-hydroxy-2,3-dihydropyridones was synthesized, and their activities as antiandrogens were tested in the human prostate cancer cell line LNCaP. Structure-activity relationship (SAR) studies resulted in the identification of a potent compound whose activity is comparable to that of MDV3100. Homology modeling and molecular mechanics were used to build a structural model of the androgen receptor ligand binding domain and to investigate the structural basis of the antagonism. The model is qualitatively consistent with the observed SAR. Moreover, the enrichment plot shows that screening with the model performs significantly better than random screening. Therefore, the model probably represents a realistic conformation of the antagonist form and can be utilized for structure-based design of novel antiandrogens.

  DOI：

  10.1021/jm301714s

文献信息

• DIHYDROPYRIDONE UREAS AS P2X7 MODULATORS
  申请人：Brotherton-Pleiss Christine E.

  公开号：US20100160388A1

  公开（公告）日：2010-06-24

  Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor.

  公式I的化合物：或其药用可接受的盐，其中m、n、R1、R2、R3、R4和R5按本文件定义。还公开了制造这些化合物的方法以及使用这些化合物治疗与P2X7嘌呤能受体相关疾病的方法。
• DIHYDROPYRIDONE AMIDES AS P2X7 MODULATORS
  申请人：Lopez-Tapia Francisco Javier

  公开号：US20100160387A1

  公开（公告）日：2010-06-24

  Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor.

  式I的化合物： 或其药用可接受的盐，其中m、n、R1、R2、R3、R4和R5如本文所定义。还公开了制备这些化合物的方法，并将这些化合物用于治疗与P2X7嘌呤受体相关的疾病。
• One pot solid phase synthesis of 2-substituted 2,3-dihydropyridin-4(1H)-ones on Rinkamide-resin
  作者：Michael Sax、Stefanie Berning、Bernhard Wünsch

  DOI：10.1016/j.tet.2004.10.031

  日期：2005.1

  A novel solid phase synthesis of 2-substituted 2,3-dihydropyridin-4(1H)-ones using Rinkamide-polystyrene-resin is described. The key step involves a hetero-Diels–Alder reaction of Danishefsky's diene with solid phase bound imines, which was carefully optimized. Using this method even ketones are transformed into 2,2-disubstituted dihydropyridones.

  描述了一种新的使用Rinkamide-聚苯乙烯树脂固相合成2-取代的2,3-二氢吡啶-4（1 H）-的方法。关键步骤涉及Danishefsky的二烯与固相键合的亚胺的杂Diels-Alder反应，该反应经过精心优化。使用该方法，甚至将酮转化为2，2-二取代的二氢吡啶酮。
• AgOTf-Catalyzed Aza-Diels–Alder Reactions of Danishefsky's Diene with Imines in Water
  作者：Catherine Loncaric、Kei Manabe、Shū Kobayashi

  DOI：10.1002/adsc.200390052

  日期：2003.4

  Aza-Diels–Alder reactions of Danishefsky's diene with imines in water took place smoothly in the presence of a catalytic amount of silver triflate to afford dihydro-4-pyridones in high yields. The silver triflate-catalyzed three-component reactions starting from aldehydes, amines, and Danishefsky's diene were also performed efficiently. In the three-component reactions with benzaldehyde, the addition

  在催化量的三氟甲磺酸银存在下，Danishefsky的二烯与亚胺在水中的Aza-Diels-Alder反应平稳进行，从而以高收率提供二氢-4-吡啶酮。从醛，胺和Danishefsky的二烯开始的三氟甲磺酸银催化的三组分反应也得到了有效地进行。在与苯甲醛的三组分反应中，发现添加非离子表面活性剂是有效的。
• Lewis Base Catalyzed Aza-Diels-Alder Type Reactions between Danishefsky’s Dienes in the Presence of Lewis Base Catalysts. An Efficient Method for the Synthesis of Substituted 2,3-Dihydropyridin-4-ones
  作者：Takayuki Kitazawa、Yuji Maruyama、Teruaki Mukaiyama

  DOI：10.3987/com-07-s(u)65

  日期：——

  Aza-Diels-Alder type reactions of various imines with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (Danishefsky's diene) derivatives catalyzed by Lewis bases such as lithium methoxide are described. The reaction proceeds via a stepwise pathway, i.e. first by an imino-aldol reaction followed by the acid mediated annulation to afford the corresponding 2,3-dihydropyridin-4-ones in high yields. An appropriate

  描述了各种亚胺与 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (Danishefsky's diene) 衍生物的 Aza-Diels-Alder 型反应，这些反应由 Lewis 碱如甲醇锂催化。该反应通过逐步途径进行，即首先通过亚氨基-羟醛反应，然后是酸介导的环化，以高产率提供相应的2,3-二氢吡啶-4-酮。An appropriate choice of the substituents on nitrogen plays important roles both in addition of the silyl enolates and in the subsequent annulation to form the desired cycloadducts.