Ethyl 2,4-dimethyl-5-oxo-5H-<1>benzopyrano<4,3-b>pyridine-3-carboxylate | 112010-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Ethyl 2,4-dimethyl-5-oxo-5H-<1>benzopyrano<4,3-b>pyridine-3-carboxylate
• 英文别名: ethyl 2,4-dimethyl-5-oxo-5H-chromeno[4,3-b]pyridine-3-carboxylate；1,3-Dimethyl-10-oxo-10H-9-oxa-4-aza-phenanthrene-2-carboxylic acid ethyl ester；ethyl 2,4-dimethyl-5-oxochromeno[4,3-b]pyridine-3-carboxylate
• CAS: 112010-36-3
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: CBBHEFALSKDVEG-UHFFFAOYSA-N

物化性质

• 熔点：
  114-117 °C(Solv: ethanol (64-17-5))
• 沸点：
  481.9±45.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Dimethyl 2-(2-methoxyphenyl)-4,6-dimethylpyridine-3,5-dicarboxylate 在 盐酸 、 氢溴酸 作用下， 反应 2.0h， 生成 Ethyl 2,4-dimethyl-5-oxo-5H-<1>benzopyrano<4,3-b>pyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis of Dialkyl 2-(2-Hydroxyphenyl)-4,6-dimethyl-1,2-dihydropyridine-3,5-dicarboxylates and Alkyl 2,4-Dimethyl-5-oxo-5H-[1]benzopyrano[4,3-b]-pyridine-3-carboxylates

  摘要：

  2-羟基苯甲醛与3-氧代丁酸酯和过量氨在室温下的醋酸中反应，生成二烷基2-(2-羟基苯基)-4,6-二甲基-1,2-二氢吡啶-3,5-二羧酸酯及其2-(3,5-二烷氧羧基-4,6-二甲基-1,2,3-三氢吡啶离子-2-基)-苯氧负离子。对这些化合物的温和氧化伴随有内酯化，形成之前被错误表述的烷基2,4-二甲基-5-氧代-5H-[1]苯并吡喃[4,3-b]吡啶-3-羧酸酯。其他o-取代苯甲醛与烷基3-氨基克罗通酸酯在室温下的醋酸中反应同样生成二烷基2-芳基-4,6-二甲基-1,2-二氢吡啶-3,5-二羧酸酯，以及常见的1,4-二氢吡啶汉兹施酯。

  DOI：

  10.1055/s-1987-27984

文献信息

• Combined experimental and computational investigations of the fluorosolvatochromism of chromeno[4,3-b]pyridine derivatives: Effect of the methoxy substitution
  作者：Mohanad Shkoor、Vandana Thotathil、Raed M. Al-Zoubi、Haw-Lih Su、Abdulilah Dawoud Bani-Yaseen

  DOI：10.1016/j.saa.2023.123210

  日期：2023.12

  conducted on the spectral properties of chromeno[4,3-b]pyridine derivatives, owing to their potential applications in sensing, optoelectronic devices, and drug discovery. This study presents a comprehensive investigation into the fluorosolvatochromism of selected chromeno[4,3-b]pyridine derivatives, with a particular emphasis on the impact of methoxy substitution. Three derivatives were synthesized

  由于色并[4,3-b]吡啶衍生物在传感、光电器件和药物发现方面的潜在应用，人们对其光谱特性进行了广泛的研究。本研究对选定的色并[4,3-b]吡啶衍生物的氟溶剂变色现象进行了全面研究，特别强调甲氧基取代的影响。合成了三种衍生物并进行了光谱分析：作为母体化合物的色并[4,3-b]吡啶-3-羧酸酯(I)，及其7-甲氧基(II)和8-甲氧基(III)取代的衍生物。 所有衍生物的紫外-可见吸收光谱均表现出宽频带，最大吸收波长不受周围介质的影响。然而，在它们之间观察到不同的荧光特性。具体而言，衍生物II表现出显着的荧光，而衍生物I和III则没有表现出荧光特性。此外，衍生物 II 表现出的荧光光谱受介质极性的显着影响。为了深入研究氟溶剂化显色行为，我们使用具有不同极性和氢键能力的各种纯溶剂进行了全面分析。获得的结果显示出显着的正氟溶剂变色现象，随着溶剂极性的增加，荧光光谱发生红移。为了了解溶质和溶剂之间的特异性和非特异性相互作用如何影响
• On the one pot syntheses of chromeno[4,3-b]pyridine-3-carboxylate and chromeno[3,4-c]pyridine-3-carboxylate and dihydropyridines
  作者：Patricio A. Navarrete-Encina、Ricardo Salazar、Christian Vega-Retter、Karina Pérez、Juan A. Squella、Luis J. Nuñez-Vergara

  DOI：10.1590/s0103-50532010000300003

  日期：——

  Substituted chromenos, dihydropyridines and pyridines have been important in the syntheses of compounds having interesting pharmacological properties. Therefore, we found of interest to synthesize chromenopyridines and chromenodihydropyridines (i.e., fused chromeno and dihydropyridine or pyridine rings) to further study their biological activity. Here, we propose one-pot syntheses for substituted ethyl-2,4-dimethyl-5-oxo-5H-chromeno[4,3-b]pyridine-3-carboxylates, ethyl-2,4-dimethyl-5-oxo-5H-chromeno[3,4-c]pyridine-3-carboxylates and their respective 1,4-dihydropyridines based on a modified Hantzsch pyridine synthesis using 2-hydroxyaryl aldehydes, with electron withdrawing and electron donating groups on the phenyl ring, as starting reactants. Sixteen compounds were synthesized by the described method and fully characterized. An average yield of 37% was obtained for the different derivatives.
• OCALLAGHAN C. N., SYNTHESIS,(1987) N 5, 499-503
  作者：OCALLAGHAN C. N.

  DOI：——

  日期：——
• Synthesis of Dialkyl 2-(2-Hydroxyphenyl)-4,6-dimethyl-1,2-dihydropyridine-3,5-dicarboxylates and Alkyl 2,4-Dimethyl-5-oxo-5<i>H</i>-[1]benzopyrano[4,3-<i>b</i>]-pyridine-3-carboxylates
  作者：C. N. O'Callaghan

  DOI：10.1055/s-1987-27984

  日期：——

  The reaction of 2-hydroxybenzaldehydes with 3-oxobutanoic esters and excess ammonia in acetic acid at room temperature yields dialkyl 2-(2-hydroxyphenyl)-4,6-dimethyl-1,2-dihydropyridine-3,5-dicarboxylates and their 2-(3,5-dialkoxycarbonyl-4,6-dimethyl-1,2,3-trihydropyridinium-2-yl)-phenoxide zwitterions. Mild oxidation of these compounds is accompanied by lactonisation, with formation of alkyl 2,4-dimethyl-5-oxo-5H-[1]benzopyrano[4,3-b]pyridine-3-carboxylates, which had previously been incorrectly formulated. Reaction of other o-substituted benzaldehydes with alkyl 3-aminocrotonates in acetic acid at room temperature also yields dialkyl 2-aryl-4,6-dimethyl-1,2-dihydropyridine-3, 5-dicarboxylates, as well as the normal 1,4-dihydropyridine Hantzsch esters.

  2-羟基苯甲醛与3-氧代丁酸酯和过量氨在室温下的醋酸中反应，生成二烷基2-(2-羟基苯基)-4,6-二甲基-1,2-二氢吡啶-3,5-二羧酸酯及其2-(3,5-二烷氧羧基-4,6-二甲基-1,2,3-三氢吡啶离子-2-基)-苯氧负离子。对这些化合物的温和氧化伴随有内酯化，形成之前被错误表述的烷基2,4-二甲基-5-氧代-5H-[1]苯并吡喃[4,3-b]吡啶-3-羧酸酯。其他o-取代苯甲醛与烷基3-氨基克罗通酸酯在室温下的醋酸中反应同样生成二烷基2-芳基-4,6-二甲基-1,2-二氢吡啶-3,5-二羧酸酯，以及常见的1,4-二氢吡啶汉兹施酯。