Ethyl 2,4-dimethyl-5-oxo-3,10b-dihydro-5H-<1>benzopyrano<3,4-c>pyridine-1-carboxylate | 94454-63-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: Ethyl 2,4-dimethyl-5-oxo-3,10b-dihydro-5H-<1>benzopyrano<3,4-c>pyridine-1-carboxylate
• 英文别名: 1-ethoxycarbonyl-2,4-dimethylcoumarin[3,4-c]dihydropyridine；ethyl 2,4-dimethyl-5-oxo-5H-chromeno[3,4-c]dihydropyridine-1-carboxylate；3,10b-Dihydro-2,4-dimethyl-5-oxo-5H[1]benzo-pyrano[3,4-c]pyridine-1-carboxylic acid ethyl ester；Ethyl 3,10B-dihydro-2,4-dimethyl-5-oxo-5H-(1)benzopyrano(3,4-c)pyridine-1-carboxylate；ethyl 2,4-dimethyl-5-oxo-3,10b-dihydro-5H-chromeno[3,4-c]pyridine-1-carboxylate；ethyl 2,4-dimethyl-5-oxo-3,10b-dihydrochromeno[3,4-c]pyridine-1-carboxylate
• CAS: 94454-63-4
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: APADKEOVXFGZAW-UHFFFAOYSA-N

物化性质

• 熔点：
  275-277 °C
• 沸点：
  436.0±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 水杨醛 在 ammonium hydroxide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.25h， 以12%的产率得到Ethyl 2,4-dimethyl-5-oxo-3,10b-dihydro-5H-<1>benzopyrano<3,4-c>pyridine-1-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

• Synthesis of tricarbonylchromium complexes of 4-aryl-1,4-dihydropyridines
  作者：Adeleh Moshtaghi Zonouz、Mina Abkar Aras、Nasrin Abuali

  DOI：10.1007/s11243-013-9698-4

  日期：2013.4

  Tricarbonylchromium complexes of 4-aryl-1,4-dihydropyridines have been synthesized both under standard thermodynamic conditions using Cr(CO)6 and under milder complexation conditions using more labile [Cr(CO)3(NH3)3] and (η6-naphthalene)Cr(CO)3. Selective complexation of the Cr(CO)3 on the aryl ring in the presence of a 1,4-dihydropyridine ring was achieved.Graphical Abstract

  4-芳基-1,4-二氢吡啶的三羰基铬配合物已在使用 Cr(CO)6 的标准热力学条件下和使用更不稳定的 [Cr(CO)3(NH3)3] 和 (η6-naphthalene )Cr(CO)3。在 1,4-二氢吡啶环的存在下，实现了芳环上 Cr(CO)3 的选择性络合。
• 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。
• 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.
• Substituted and bridged pyridines useful as pharmaceutical agents
  申请人：Merck & Co., Inc.

  公开号：EP0163238B1

  公开（公告）日：1991-07-24
• OCALLAGHAN C. N., SYNTHESIS,(1987) N 5, 499-503
  作者：OCALLAGHAN C. N.

  DOI：——

  日期：——