ethyl 5-(2-hydroxybenzoyl)-2-oxo-1-phenethyl-1,2-dihydropyridine-3-carboxylate | 1432594-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5-(2-hydroxybenzoyl)-2-oxo-1-phenethyl-1,2-dihydropyridine-3-carboxylate
• 英文别名: Ethyl 5-(2-hydroxybenzoyl)-2-oxo-1-(2-phenylethyl)pyridine-3-carboxylate；ethyl 5-(2-hydroxybenzoyl)-2-oxo-1-(2-phenylethyl)pyridine-3-carboxylate
• CAS: 1432594-77-8
• 化学式: C₂₃H₂₁NO₅
• 分子量: 391.423
• InChiKey: AYXTVNWIIUKANH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-(2-hydroxybenzoyl)-2-oxo-1-phenethyl-1,2-dihydropyridine-3-carboxylate 在 potassium carbonate 、 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以78%的产率得到ethyl 2,5-dioxo-1-phenethyl-2,5-dihydro-1H-chromeno[2,3-b]-pyridine-3-carboxylate
  参考文献：
  名称：

  竞争性分子内C– Cvs。C 6环稠合的2-吡啶酮合成过程中的C–O键偶联反应†

  摘要：

  有趣的竞争性C– Cvs。据报道，在N，3,5-三取代的吡啶酮上存在C-O键偶联反应。这些偶联反应提供了在具有挑战性的C 6-吡啶酮位置上选择性接近C-或O-环稠合的吡啶酮的途径。在Pd（0）条件下，通常以高收率和优异的化学选择性获得1,6- C环吡啶酮。另一方面，在由银盐促进的氧化偶联作用下获得完全的C 6-区域选择性Csp 2芳氧基化以接近5,6- O环吡啶酮。在各种实验和观察的基础上，提供了这些竞争反应的机理证据，并提出了通过自由基环化进行C-O键的形成。这些过程是在温和的反应条件下进行的，并提供了一种有效且有吸引力的方法，可选择性地获取大范围的具有生物学意义的C-芳基和O-芳基吡啶酮。

  DOI：

  10.1039/c6ob00303f
• 作为产物：
  描述：

  、 2-苯乙胺 在 cesium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到ethyl 5-(2-hydroxybenzoyl)-2-oxo-1-phenethyl-1,2-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  A versatile domino process for the synthesis of substituted 3-aminomethylene-chromanones and 2-pyridones catalyzed by CsF

  摘要：

  The addition of various primary amines onto 3-alpha,beta-unsaturated diester chromone derivative was studied under mild conditions. Basically, this reaction provided 2-pyridone-based compounds through an interesting domino 'Addition/Ring Opening/Ring Closure' process (ARORC). In this study, aniline and tryptamine series exhibited different reactivity profiles leading unexpectedly to 3-aminomethylene chromanones with or without the 2-pyridone derivatives. This constitutes the first description and study of 3-aminomethylene chromanone formation that is supposed to follow a domino process combining 'Addition/Ring Opening/Ring Closure by Oxa-Michael addition' (ARORCOM). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.096

文献信息

• Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction
  作者：Tej Narayan Poudel、Yong Rok Lee、Sung Hong Kim

  DOI：10.1039/c5gc01526j

  日期：——

  An eco-friendly protocol for diverse and functionalized 2-pyridone derivatives via a multicomponent reaction under catalyst- and solvent-free conditions has been developed.

  已经开发了一种在无催化剂和无溶剂条件下通过多组分反应进行多样且功能化的2-吡啶酮衍生物的环保方案。
• Compounds and methods for inhibiting EMT pathways to treat cancer, organ fibrosis and metabolic disorders
  申请人：University of Pittsburgh—Of the Commonwealth System of Higher Education

  公开号：US11078159B2

  公开（公告）日：2021-08-03

  A compound, or a pharmaceutically acceptable salt or isomer thereof, of Formula I: wherein R is hydrogen, alkyl, substituted alkyl, alkenyl, or substituted alkenyl; R1 is hydrogen, alkoxy, or substituted alkoxy; R2 is hydrogen, alkyl, or substituted alkyl; and R3 is hydrogen, alkyl, or substituted alkyl.

  式 I 的化合物或其药学上可接受的盐或异构体： 其中 R 是氢、烷基、取代烷基、烯基或取代烯基； R1 是氢、烷氧基或取代的烷氧基 R2 是氢、烷基或取代烷基；和 R3 是氢、烷基或取代的烷基。
• KR101795283
  申请人：——

  公开号：——

  公开（公告）日：——
• COMPOUNDS AND METHODS FOR INHIBITING EMT PATHWAYS TO TREAT CANCER, ORGAN FIBROSIS AND METABOLIC DISORDERS
  申请人：University of Pittsburgh - Of the Commonwealth System of Higher Education

  公开号：US20220017466A1

  公开（公告）日：2022-01-20

  A compound, or a pharmaceutically acceptable salt or isomer thereof, of Formula I: wherein R is hydrogen, alkyl, substituted alkyl, alkenyl, or substituted alkenyl; R 1 is hydrogen, alkoxy, or substituted alkoxy; R 2 is hydrogen, alkyl, or substituted alkyl; and R 3 is hydrogen, alkyl, or substituted alkyl.
• A versatile domino process for the synthesis of substituted 3-aminomethylene-chromanones and 2-pyridones catalyzed by CsF
  作者：Catalin Pintiala、Ata Martin Lawson、Sébastien Comesse、Adam Daïch

  DOI：10.1016/j.tetlet.2013.03.096

  日期：2013.5

  The addition of various primary amines onto 3-alpha,beta-unsaturated diester chromone derivative was studied under mild conditions. Basically, this reaction provided 2-pyridone-based compounds through an interesting domino 'Addition/Ring Opening/Ring Closure' process (ARORC). In this study, aniline and tryptamine series exhibited different reactivity profiles leading unexpectedly to 3-aminomethylene chromanones with or without the 2-pyridone derivatives. This constitutes the first description and study of 3-aminomethylene chromanone formation that is supposed to follow a domino process combining 'Addition/Ring Opening/Ring Closure by Oxa-Michael addition' (ARORCOM). (C) 2013 Elsevier Ltd. All rights reserved.