methyl 1-benzyl-2-oxo-1,2-dihydropyridine-3-carboxylate | 400082-66-8

• 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: methyl 1-benzyl-2-oxo-1,2-dihydropyridine-3-carboxylate
• 英文别名: methyl 1-benzyl-2-oxo-1,2-dihydronicotinate；methyl 1-benzyl-2-oxopyridine-3-carboxylate
• CAS: 400082-66-8
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: CHWAGTQIWFARSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 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：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-2-oxo-1,2-dihydropyridine-3-carboxylate 在 lithium hydroxide monohydrate 、 水 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1-benzyl-N-(2,6-dioxopiperidin-3-yl)-2-oxo-1,2-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  WO2020006233A5

  摘要：

  公开号：

  WO2020006233A5
• 作为产物：
  描述：

  2-氯烟酸甲酯 在 sodium 作用下， 反应 26.0h， 生成 methyl 1-benzyl-2-oxo-1,2-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Discovery of pyridine-2-ones as novel class of multidrug resistance (MDR) modulators: First structure–activity relationships

  摘要：

  A novel facile synthesis led to pyridine-2-one target structures of which first series with varying substituents have been yielded and biologically characterized as novel multidrug resistance (MDR) modulators inhibiting P-glycoprotein (P-gp). Structure-activity relationships prove a dependency of the MDR-modulating properties from the kind and positioning of hydrogen bond acceptor functions within the molecular skeleton. Cyano functions turned out as biologically effective substituents for a potential hydrogen bonding to the protein target structure. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.005

文献信息

• Monocyclic heterocycles as kinase inhibitors
  申请人：Borzilleri M. Robert

  公开号：US20050245530A1

  公开（公告）日：2005-11-03

  The present invention is directed to compounds having the formula and methods for using them for the treatment of cancer.

  本发明涉及具有以下公式化合物的用途以及使用它们治疗癌症的方法。
• Synthesis of the core ring system of awajanomycin from N-Boc-3-methoxycarbonyl-2-pyridinone
  作者：Kou Hiroya、Kei Kawamoto、Kiyofumi Inamoto、Takao Sakamoto、Takayuki Doi

  DOI：10.1016/j.tetlet.2009.02.141

  日期：2009.5

  configuration has been determined. We report the synthesis of the core ring system of awajanomycin, which includes: (i) regioselective addition of the acetate unit onto C4-position of N-Boc-3-methoxycarbonyl-2-pyridinone; (ii) stereoselective installation of a hydroxyl group on C3-position; and (iii) stereo- and regioselective epoxide-opening reaction by Me3Al.

  从海洋来源的真菌中分离出的阿波那霉素具有独特的结构特征和针对A549细胞的细胞毒活性。由于其独特的结构，尚无完整的合成报道，也没有确定相对立体化学或绝对构型。我们报道了阿维霉素的核心环系统的合成，该合成包括：（i）将乙酸酯单元区域选择性加成到N -Boc-3-甲氧基羰基-2-吡啶酮的C4位上；（ii）在C3-位上立体选择性地安装羟基；（iii）由Me 3 Al进行的立体和区域选择性环氧化物的开放反应。
• Introduction of the Acetate Unit to the 2-Pyridinone Ring System and Its Application to the Synthesis of (20<i>S</i>)-Camptothecin DE Ring System
  作者：Kou Hiroya、Kei Kawamoto、Takao Sakamoto

  DOI：10.1055/s-2006-950433

  日期：2006.9

  The DE ring system of (20S)-camptothecin had been ­prepared from commercially available nicotinic acid in six steps ­utilizing the nucleophilic addition reaction of the silyl ketene acetal to the pyridinone ring as a key step.

  (20S)-喜树碱的 DE 环系统是利用硅酮缩醛与吡啶酮环的亲核加成反应作为关键步骤，通过六个步骤从市售烟酸中制备出来的。
• MONOCYCLIC HETEROCYCLES AS KINASE INHIBITORS
  申请人：Borzilleri Robert M.

  公开号：US20090054436A1

  公开（公告）日：2009-02-26

  The present invention is directed to compounds having the formula and methods for using them for the treatment of cancer.

  本发明涉及具有以下结构式的化合物及其用于癌症治疗的方法。
• Regioselective [2 + 1] photocycloaddition of 2-pyridones with diazo compounds
  作者：Fengya He、Ziyi Sun、Chenyue Li、Zibin Jiang、Hui Miao、Qinglin Li、Chenggui Wu

  DOI：10.1039/d3ob01354e

  日期：——

  Herein, we report a novel regioselective [2 + 1] cyclization reaction of 2-pyridones with carbenes generated in situ via visible light irradiation, without the requirement for catalysts or additives. The diverse functional groups of 2-pyridones and diazo compounds exhibit good tolerance, enabling the rapid synthesis of highly valuable cyclopropanated dihydro-2-pyridone scaffolds with exceptional regio-

  在此，我们报道了一种新型的2-吡啶酮与卡宾的区域选择性[2 + 1]环化反应，通过可见光照射原位生成，无需催化剂或添加剂。2-吡啶酮和重氮化合物的多种官能团表现出良好的耐受性，能够快速合成具有优异区域选择性和立体选择性的高价值环丙烷化二氢-2-吡啶酮支架。此外，DFT 计算为反应中观察到的区域选择性和立体选择性提供了全面的解释。