Ethyl 2,4-dimethyl-5-oxo-5H-<1>benzopyrano<3,4-c>pyridine-1-carboxylate | 94454-64-5

• 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<3,4-c>pyridine-1-carboxylate
• 英文别名: 1-ethoxycarbonyl-2,4-dimethylcoumarin[3,4-c]pyridine；ethyl 2,4-dimethyl-5-oxo-5H-chromeno[3,4-c]pyridine-1-carboxylate；4-(2-hydroxy-phenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid ethyl ester lactone；4-(2-Hydroxy-phenyl)-2,6-dimethyl-pyridin-3,5-dicarbonsaeure-aethylester-lacton；ethyl 2,4-dimethyl-5-oxochromeno[3,4-c]pyridine-1-carboxylate
• CAS: 94454-64-5
• 化学式: C₁₇H₁₅NO₄
• mdl: MFCD05857652
• 分子量: 297.31
• InChiKey: YPQVJEXYFVCXMD-UHFFFAOYSA-N

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

• 作为反应物：
  描述：

  Ethyl 2,4-dimethyl-5-oxo-5H-<1>benzopyrano<3,4-c>pyridine-1-carboxylate 、 氯化亚砜 生成 2,4-dimethyl-7-oxa-3-azatetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14),8,10,12-hexaene-6,15-dione
  参考文献：
  名称：

  PASANEN, PAAVO;NEURONEN, KARI, ANN. ACAD. SCI. FENN. SER. A 2,(1990) N27, C. 253-254

  摘要：

  DOI：
• 作为产物：
  描述：

  Ethyl 2,4-dimethyl-5-oxo-3,10b-dihydro-5H-<1>benzopyrano<3,4-c>pyridine-1-carboxylate 在 tert-butylammonium hexafluorophosphate(V) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 2,4-dimethyl-5-oxo-5H-<1>benzopyrano<3,4-c>pyridine-1-carboxylate
  参考文献：
  名称：

  杂化化合物的合成与电化学氧化：二氢吡啶融合的香豆素

  摘要：

  本文合成了一系列六个六氢吡啶融合的香豆素，并在二甲基甲酰胺（DMF）中进行了电化学表征。 玻碳电极（GCE）上的二氢吡啶环氧化生成稠合杂环化合物显示出一个单一的阳极峰。氧化电势值与9位取代基效应相关性很好。如计时电流法所确定的，整个氧化机理涉及2-电子和2-质子。 受控电位电解，然后进行UV-可见光谱分析，证明在DMF中，二氢吡啶融合的香豆素被电化学氧化，生成芳香族吡啶衍生物。ESR实验光谱显示出三重态，这是由于C中心的二氢吡啶基团被N-叔丁胺-α-苯基硝酮（PBN）捕获。二氢吡啶融合的香豆素的超精细偶合常数值（a N）高于非融合的香豆素的相应值。这些结果可能是由于二氢吡啶部分与香豆素环的偶联在分裂常数上的影响。

  DOI：

  10.1016/j.electacta.2014.01.137

文献信息

• 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。
• Dihydropyridine-fused and pyridine-fused coumarins: Reduction on a glassy carbon electrode in dimethylformamide
  作者：Luis J. Nuñez-Vergara、V. Pardo-Jiménez、C. Barrientos、C.A. Olea-Azar、P.A. Navarrete-Encina、J.A. Squella

  DOI：10.1016/j.electacta.2012.08.088

  日期：2012.12

  pyridine-fused coumarins were synthesised and electrochemically characterised in aprotic medium. In both series, the most easily reducible groups were the endocyclic carbonyl groups. The electrochemical mechanism for both types of compounds is strongly dependent on the experimental time-scale. Cyclic voltammetric (CV) reduction on a glassy carbon electrode (GCE) of the endocyclic carbonyl group of d

  在这项研究中，合成了两个系列的二氢吡啶-融合和吡啶-融合的香豆素，并在非质子介质中进行了电化学表征。在这两个系列中，最易还原的基团是环内羰基。两种类型化合物的电化学机理都在很大程度上取决于实验时间尺度。二氢吡啶基融合的香豆素内环羰基的玻碳电极（GCE）上的循环伏安（CV）还原涉及具有两个电子转移步骤的ECEC机制，该步骤与化学反应相结合以生成相应的半缩醛衍生物。就吡啶融合的香豆素而言，内环羰基的CV还原涉及EEC机制。ESR研究表明，仅对吡啶融合的衍生物存在稳定的中间体。我们的理论研究表明，自由基物种的自旋密度图主要在香豆素环内离域，表明环内羰基的还原。在二氢吡啶稠合衍生物的情况下，二氢吡啶环的弱酸性氢通过父子型反应使自由基失稳。
• 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.
• PASANEN, PAAVO;NEURONEN, KARI, ANN. ACAD. SCI. FENN. SER. A 2,(1990) N27, C. 253-254
  作者：PASANEN, PAAVO、NEURONEN, KARI

  DOI：——

  日期：——
• OCALLAGHAN C. N., SYNTHESIS,(1987) N 5, 499-503
  作者：OCALLAGHAN C. N.

  DOI：——

  日期：——