5-Acetyl-4-ethoxycarbonylmethyl-2-(4-fluoro-phenyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester | 141501-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-Acetyl-4-ethoxycarbonylmethyl-2-(4-fluoro-phenyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester
• 英文别名: ethyl 5-acetyl-4-(2-ethoxy-2-oxoethyl)-2-(4-fluorophenyl)-6-oxo-1H-pyridine-3-carboxylate
• CAS: 141501-55-5
• 化学式: C₂₀H₂₀FNO₆
• 分子量: 389.38
• InChiKey: AJFHHZDZVXIPGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Acetyl-4-ethoxycarbonylmethyl-2-(4-fluoro-phenyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以90%的产率得到3-(4-Fluoro-phenyl)-6,8-dihydroxy-1-oxo-1,2-dihydro-isoquinoline-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  A Versatile New Method for Synthesis of Isoquinolines; 6,8-Dihydroxyisoquinoline Derivatives from 6-Methyl-1,3-oxazin-4-ones

  摘要：

  A versatile method for synthesis of isoquinolone derivatives (4a-h) from 2-substituted 6-methyl-4H-1,3-oxazin-4-ones (1a-h) is described. Transformation of 1a-h with diethyl acetonedicarboxylate (2) in the presence of potassium tert-butoxide afforded 6-substituted 3-acetyl-5-ethoxycarbonyl-4-ethoxycarbonylmethylene-2-pyridones (3a-h) in excellent yields. Dieckmann-type cyclization of 3a-h with sodium ethoxide in ethanol produced the corresponding isoquinolone derivatives (4a-h) in good yields, respectively.

  DOI：

  10.3987/com-91-s75
• 作为产物：
  描述：

  2-(4-Fluoro-phenyl)-6-methyl-[1,3]oxazin-4-one 、 1,3-丙酮二羧酸二乙酯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到5-Acetyl-4-ethoxycarbonylmethyl-2-(4-fluoro-phenyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  A Versatile New Method for Synthesis of Isoquinolines; 6,8-Dihydroxyisoquinoline Derivatives from 6-Methyl-1,3-oxazin-4-ones

  摘要：

  A versatile method for synthesis of isoquinolone derivatives (4a-h) from 2-substituted 6-methyl-4H-1,3-oxazin-4-ones (1a-h) is described. Transformation of 1a-h with diethyl acetonedicarboxylate (2) in the presence of potassium tert-butoxide afforded 6-substituted 3-acetyl-5-ethoxycarbonyl-4-ethoxycarbonylmethylene-2-pyridones (3a-h) in excellent yields. Dieckmann-type cyclization of 3a-h with sodium ethoxide in ethanol produced the corresponding isoquinolone derivatives (4a-h) in good yields, respectively.

  DOI：

  10.3987/com-91-s75

文献信息

• A Versatile New Method for Synthesis of Isoquinolines; 6,8-Dihydroxyisoquinoline Derivatives from 6-Methyl-1,3-oxazin-4-ones
  作者：Yutaka Yamamoto、Yasuo Morita、Osamu Ohmukai

  DOI：10.3987/com-91-s75

  日期：——

  A versatile method for synthesis of isoquinolone derivatives (4a-h) from 2-substituted 6-methyl-4H-1,3-oxazin-4-ones (1a-h) is described. Transformation of 1a-h with diethyl acetonedicarboxylate (2) in the presence of potassium tert-butoxide afforded 6-substituted 3-acetyl-5-ethoxycarbonyl-4-ethoxycarbonylmethylene-2-pyridones (3a-h) in excellent yields. Dieckmann-type cyclization of 3a-h with sodium ethoxide in ethanol produced the corresponding isoquinolone derivatives (4a-h) in good yields, respectively.