8-Ethoxy-1,3-dimethyl-10-oxo-10H-9-oxa-4-aza-phenanthrene-2-carboxylic acid ethyl ester | 112010-40-9

• 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: 8-Ethoxy-1,3-dimethyl-10-oxo-10H-9-oxa-4-aza-phenanthrene-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 7-ethoxy-2,4-dimethyl-5-oxochromeno[4,3-b]pyridine-3-carboxylate
• CAS: 112010-40-9
• 化学式: C₁₉H₁₉NO₅
• 分子量: 341.364
• InChiKey: SKFBVBNAJRCBAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-乙氧基水杨醛 、 (E)-3-氨基巴豆酸乙酯 以15%的产率得到
  参考文献：
  名称：

  OCALLAGHAN C. N., SYNTHESIS,(1987) N 5, 499-503

  摘要：

  DOI：

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

  DOI：——

  日期：——