ethyl 9-bromo-2,4-dimethyl-5-oxo-5H-chromeno[3,4-c]pyridine-1-carboxylate | 213537-35-0

• 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 9-bromo-2,4-dimethyl-5-oxo-5H-chromeno[3,4-c]pyridine-1-carboxylate
• 英文别名: Ethyl 9-bromo-2,4-dimethyl-5-oxochromeno[3,4-c]pyridine-1-carboxylate
• CAS: 213537-35-0
• 化学式: C₁₇H₁₄BrNO₄
• 分子量: 376.206
• InChiKey: SGZVGQZONYLUPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 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：

  ethyl 9-bromo-2,4-dimethyl-5-oxo-5H-chromeno[3,4-c]dihydropyridine-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 9-bromo-2,4-dimethyl-5-oxo-5H-chromeno[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

• 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.