2-methyl-5-(2-hydroxybenzoyl)nicotinic acid methyl ester | 78831-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-5-(2-hydroxybenzoyl)nicotinic acid methyl ester
• 英文别名: Methyl 5-(2-hydroxybenzoyl)-2-methylpyridine-3-carboxylate
• CAS: 78831-18-2
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: KRMSOOAERZYDFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰乙酸甲酯 在 ammonium acetate 、 sodium acetate 、 乙酸酐 作用下， 反应 2.25h， 生成 2-methyl-5-(2-hydroxybenzoyl)nicotinic acid methyl ester
  参考文献：
  名称：

  Solvent-free synthesis of functionalized pyridine derivatives using Wells-Dawson heteropolyacid as catalyst

  摘要：

  Wells-Dawson heteropolyacids (H(6)P(2)W(18)O(62)center dot 24H(2)O) were used as catalysts in the Hantzsch-like multi-component condensation reaction with 3-formylchromones as aldehyde component, a beta-ketoester and ammonium acetate, under solvent-free conditions at 80 degrees C. Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60-99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines. (C) 2011 Elsevier I.td. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.048

文献信息

• Simple and ecofriendly synthesis of dihydropyrimidinones (thiones), dihydropyridines, and pyridines using 3-formylchromones as substrates assisted by a recyclable Preyssler heteropolyacid
  作者：Laura M. Sanchez、Gustavo Pasquale、Ángel Sathicq、Diego Ruiz、Jorge Jios、Andrea L. Ferreira de Souza、Gustavo P. Romanelli

  DOI：10.1002/hc.21340

  日期：2016.9

  Several dihydropyrimidinones/thiones, 1,4-dihydropyridines, and pyridine derivatives were prepared in very good yields and purity values. The corresponding reactions were carried out by employing a bulk Preyssler heteropolyacid H14[NaP5W29MoO110] as an efficient and recyclable catalyst. The preparation of pyridine derivatives was carried out not through a usual procedure, i.e., the opening of the γ-pyrone

  以非常好的产率和纯度值制备了几种二氢嘧啶酮/硫酮、1,4-二氢吡啶和吡啶衍生物。相应的反应是通过使用本体 Preyssler 杂多酸 H14[NaP5W29MoO110] 作为有效且可回收的催化剂进行的。吡啶衍生物的制备不是通过通常的程序进行的，即3-甲酰基色酮的γ-吡喃酮环的开环。通常，反应在 80°C 的无溶剂条件下进行，反应时间很短。
• Hass, Georges; Stanton, James L.; Sprecher, Andreas von, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 607 - 612
  作者：Hass, Georges、Stanton, James L.、Sprecher, Andreas von、Wenk, Paul

  DOI：——

  日期：——
• HAAS G.; STANTON J. L.; SPRECHER A. VON; WENK P., J. HETEROCYCL. CHEM., 1981, 18, NO 3, 607-612
  作者：HAAS G.、 STANTON J. L.、 SPRECHER A. VON、 WENK P.

  DOI：——

  日期：——
• Solvent-free synthesis of functionalized pyridine derivatives using Wells-Dawson heteropolyacid as catalyst
  作者：Laura M. Sanchez、Ángel G. Sathicq、Jorge L. Jios、Graciela T. Baronetti、Horacio J. Thomas、Gustavo P. Romanelli

  DOI：10.1016/j.tetlet.2011.06.048

  日期：2011.8

  Wells-Dawson heteropolyacids (H(6)P(2)W(18)O(62)center dot 24H(2)O) were used as catalysts in the Hantzsch-like multi-component condensation reaction with 3-formylchromones as aldehyde component, a beta-ketoester and ammonium acetate, under solvent-free conditions at 80 degrees C. Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60-99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines. (C) 2011 Elsevier I.td. All rights reserved.