ethyl 2-methyl-5-(2-hydroxy-5-methylbenzoyl)-pyridine-3-carboxylate | 425430-37-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-methyl-5-(2-hydroxy-5-methylbenzoyl)-pyridine-3-carboxylate
• 英文别名: Ethyl 5-(2-hydroxy-5-methylbenzoyl)-2-methylpyridine-3-carboxylate
• CAS: 425430-37-1
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: MPLCKSXTZTVXSA-UHFFFAOYSA-N

物化性质

• 沸点：
  455.6±45.0 °C(predicted)
• 密度：
  1.215±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-5-(2-hydroxy-5-methylbenzoyl)-pyridine-3-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 以97%的产率得到5-(2-hydroxy-5-methylbenzoyl)-2-methylnicotinic acid
  参考文献：
  名称：

  Reagent-controlled domino synthesis of skeletally-diverse compound collections

  摘要：

  已开发出一种高效的试剂控制方法，可通过共用底物生成高度取代的多样性骨架；因此，使用不同的脱硅试剂（如氟化铵、氟化铯和PPTS）处理共用前体，会引发不同的多米诺反应序列，分别生成高度取代的吡啶、酚和苯并吡喃；这些骨架的取代模式为文库开发提供了进一步的机会。

  DOI：

  10.1039/b717635j
• 作为产物：
  描述：

  在 氨 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以60%的产率得到ethyl 2-methyl-5-(2-hydroxy-5-methylbenzoyl)-pyridine-3-carboxylate
  参考文献：
  名称：

  苯并吡喃。第42部分†。氨存在下4-Oxo-4 H -1-苯并吡喃-3-甲醛与某些活性亚甲基化合物的反应

  摘要：

  在氨存在下的标题醛1分别与乙酰丙酮，丙二酸二乙酯和氰基乙酸乙酯，以及（或甲基）-1-苯并吡喃并[4,3 - b ]吡啶-丁-3-羧酸酯分别给出吡啶衍生物9-11 22（或23）用乙酰乙酸乙酯（或甲基）。用氨预处理的乙酰丙酮与1缩合，得到稠合的吡啶24。氨将酯6转化为吡啶13或14。22和23的铬酸氧化分别提供香豆素吡啶25和26。

  DOI：

  10.1002/jhet.5570380632

文献信息

• Benzopyrans. Part 42. Reactions of 4-Oxo-4<i>H</i>-1-benzopyran-3-carbaldehyde with some active methylene compounds in the presence of ammonia
  作者：Chandra Kanta Ghosh、Anirban Ray、Amarendra Patra

  DOI：10.1002/jhet.5570380632

  日期：2001.11

  The title aldehyde 1 in the presence of ammonia gives the pyridine derivatives 9-11 respectively with acetylacetone, diethyl malonate and ethyl cyanoacetate, and ethyl (or methyl)-l-benzopyrano[4,3-b]pyri-dine-3-carboxylate 22 (or 23) with ethyl (or methyl) acetoacetate. Acetylacetone pretreated with ammonia condenses with 1 giving the fused pyridine 24. Ammonia converts the ester 6 to the pyridine

  在氨存在下的标题醛1分别与乙酰丙酮，丙二酸二乙酯和氰基乙酸乙酯，以及（或甲基）-1-苯并吡喃并[4,3 - b ]吡啶-丁-3-羧酸酯分别给出吡啶衍生物9-11 22（或23）用乙酰乙酸乙酯（或甲基）。用氨预处理的乙酰丙酮与1缩合，得到稠合的吡啶24。氨将酯6转化为吡啶13或14。22和23的铬酸氧化分别提供香豆素吡啶25和26。
• 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。
• 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.
• Reagent-controlled domino synthesis of skeletally-diverse compound collections
  作者：Herbert Waldmann、Marc Kühn、Wei Liu、Kamal Kumar

  DOI：10.1039/b717635j

  日期：——

  An efficient reagent-controlled methodology for generating highly substituted diverse scaffolds from a common substrate has been developed; thus, treatment of a common precursor with different desilylating reagents, such as ammonium fluoride, caesium fluoride and PPTS, triggers different domino reaction sequences, yielding highly substituted pyridines, phenols and benzopyrans, respectively; the substituent patterns of these scaffolds provide further opportunities for library development.

  已开发出一种高效的试剂控制方法，可通过共用底物生成高度取代的多样性骨架；因此，使用不同的脱硅试剂（如氟化铵、氟化铯和PPTS）处理共用前体，会引发不同的多米诺反应序列，分别生成高度取代的吡啶、酚和苯并吡喃；这些骨架的取代模式为文库开发提供了进一步的机会。