Methyl 4-(4-carboxyphenyl)-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate | 177763-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 4-(4-carboxyphenyl)-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate
• 英文别名: 4-(2-Chloro-3-formyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-4-yl)benzoic acid
• CAS: 177763-78-9
• 化学式: C₁₆H₁₄ClNO₅
• 分子量: 335.744
• InChiKey: OTDBKLKJDNTCDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 4-(4-carboxyphenyl)-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以65%的产率得到Methyl 4-(4-carboxyphenyl)-6-methyl-4,7-dihydro-1H-pyrazolo<3,4-b>pyridine-5-carboxylate
  参考文献：
  名称：

  Synthesis of methyl 4-aryl-6-methyl-4,7-dihydro-1H-pyrazolo-[3,4-b]pyridine-5-carboxylates from methyl 4-aryl-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates

  摘要：

  Novel methyl 4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5 3a-e have been prepared in a two step procedure from the readily available 2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates 1a-e by treatment with the Vilsmeier-Haack reagent. Further treatment of the novel o-chloroformyl substituted methyl 1,4-dihydropyridine-5-carboxylates 2a-e with hydrazine affords the corresponding methyl pyrazolo[3,4-b]pyridine-5-carboxylates in good yields. Semiempirical calculations reveal a favoured geometry with a boat conformation in the dihydropyridine system and a planar pyrazole ring.

  DOI：

  10.1039/p19960000947
• 作为产物：
  描述：

  4-氰基苯甲醛 在 ammonium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 反应 32.5h， 生成 Methyl 4-(4-carboxyphenyl)-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis of methyl 4-aryl-6-methyl-4,7-dihydro-1H-pyrazolo-[3,4-b]pyridine-5-carboxylates from methyl 4-aryl-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates

  摘要：

  Novel methyl 4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5 3a-e have been prepared in a two step procedure from the readily available 2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates 1a-e by treatment with the Vilsmeier-Haack reagent. Further treatment of the novel o-chloroformyl substituted methyl 1,4-dihydropyridine-5-carboxylates 2a-e with hydrazine affords the corresponding methyl pyrazolo[3,4-b]pyridine-5-carboxylates in good yields. Semiempirical calculations reveal a favoured geometry with a boat conformation in the dihydropyridine system and a planar pyrazole ring.

  DOI：

  10.1039/p19960000947

文献信息

• Synthesis of methyl 4-aryl-6-methyl-4,7-dihydro-1H-pyrazolo-[3,4-b]pyridine-5-carboxylates from methyl 4-aryl-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates
  作者：Yamila Verdecia、Margarita Suárez、Alhmed Morales、Elena Rodríguez、Estael Ochoa、Leandro González、Nazario Martín、Margarita Quinteiro、Carlos Seoane、José L. Soto

  DOI：10.1039/p19960000947

  日期：——

  Novel methyl 4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5 3a-e have been prepared in a two step procedure from the readily available 2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates 1a-e by treatment with the Vilsmeier-Haack reagent. Further treatment of the novel o-chloroformyl substituted methyl 1,4-dihydropyridine-5-carboxylates 2a-e with hydrazine affords the corresponding methyl pyrazolo[3,4-b]pyridine-5-carboxylates in good yields. Semiempirical calculations reveal a favoured geometry with a boat conformation in the dihydropyridine system and a planar pyrazole ring.

表征谱图