methyl 5-cyano-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate | 67587-23-9

• 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: methyl 5-cyano-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
• 英文别名: 5-methoxycarbonyl-3-cyano-2,6-dimethyl-4(o-nitrophenyl)-1,4 dihydropyridine；3-Cyano-1,4-dihydro-2,6-dimethyl-4-(2'-nitrophenyl)-pyridin-5-carbonsaeuremethylester
• CAS: 67587-23-9
• 化学式: C₁₆H₁₅N₃O₄
• 分子量: 313.313
• InChiKey: MICCXMNEYNGTAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  470.8±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-cyano-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 在 acetic buffer 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以83%的产率得到Benzo[c][2,7]naphthyridine-1-carboxylic acid,5-amino-3,10b-dihydro-2,4-dimethyl-, methyl ester, 6-oxide
  参考文献：
  名称：

  Electrochemical behaviour of an unsymmetrical 4-(o-nitrophenyl)-1,4-dihydropyridine in protic medium

  摘要：

  The electrochemical behaviour of 3-cyano-5-methoxycarbonyl-2,6-dimethyl-4(o-nitrophenyl)-1,4-dihydropyridine and the corresponding N-methyl derivative have been investigated in hydroalcoolic medium. The 4 electron reduction leads to an amino-benzonaphtyridine N-oxide (cyclization from the reaction of the hydroxylamino group with the cyano substituent) when performed in acidic medium; in basic medium, the same reduction leads to a cyclic hydroxamic acid resulting from the condensation of the hydroxylamino group with the ester substituent. Anodic oxidations give the corresponding pyridine or pyridinium derivatives; subsequent reductions of the latter always lead to cyclic hydroxamic acids.

  DOI：

  10.1016/0040-4020(95)00057-f
• 作为产物：
  描述：

  3-氨基巴豆腈 、 硝苯啶杂质C 以 甲醇 为溶剂， 反应 18.0h， 以70%的产率得到methyl 5-cyano-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Electrochemical behaviour of an unsymmetrical 4-(o-nitrophenyl)-1,4-dihydropyridine in protic medium

  摘要：

  The electrochemical behaviour of 3-cyano-5-methoxycarbonyl-2,6-dimethyl-4(o-nitrophenyl)-1,4-dihydropyridine and the corresponding N-methyl derivative have been investigated in hydroalcoolic medium. The 4 electron reduction leads to an amino-benzonaphtyridine N-oxide (cyclization from the reaction of the hydroxylamino group with the cyano substituent) when performed in acidic medium; in basic medium, the same reduction leads to a cyclic hydroxamic acid resulting from the condensation of the hydroxylamino group with the ester substituent. Anodic oxidations give the corresponding pyridine or pyridinium derivatives; subsequent reductions of the latter always lead to cyclic hydroxamic acids.

  DOI：

  10.1016/0040-4020(95)00057-f

文献信息

• 4-[N-(Substituierte)-amino-phenyl]-substituierte 1,4-Di-(hydro)-pyridinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
  申请人：ALKALOIDA VEGYESZETI GYAR

  公开号：EP0260675A1

  公开（公告）日：1988-03-23

  Gegenstand der Erfindung sind 4-[N-(substituierte)-aminophenyl]-substituierte 1,4-Di-(hydro)-pyridinderivate der allgemeinen Formel worin R₁ für einen Alkanoylrest, einen Cycloalkanoylrest, einen Arylcarbonyl- beziehungsweise Aralkylencarbonylrest der allgemeinen Formel II, einen Trifluoracetylrest, einen Alkoxycarbonylrest der allgemeinen Formel III, einen Alkylsulfonyl- oder Phenylsulfonylrest der allgemeinen Formel IV steht, R₂ eine Cyangruppe oder einen Alkoxycarbonylrest bedeutet, R₃ für einen Alkylrest, einen Cycloalkylrest oder einen Alkoxyalkylrest steht und R₄ einen Alkylrest bedeutet, einschließlich ihrer racemischen und optisch aktiven Formen und Gemische sowie ihre Säureadditionssalze. Gegenstand der Erfindung sind auch ein Verfahren zur Herstellung dieser Verbindungen und diese enthaltende Arzneimittel.

  本发明的主题是通式为 4-[N-（取代的）-氨基苯基]-取代的 1，4-二（氢）-吡啶衍生物 其中 R₁ 是通式 II 的烷酰基、环烷酰基、芳基羰基或芳烷基羰基、三氟乙酰基、通式 III 的烷氧羰基、通式 IV 的烷基磺酰基或苯基磺酰基、 R₂ 是氰基或烷氧羰基、 R₃ 代表烷基、环烷基或烷氧基烷基，以及 R₄ 表示烷基、 包括它们的外消旋体、光学活性形式和混合物以及它们的酸加成盐。 本发明还涉及制备这些化合物和含有这些化合物的药物的工艺。
• O'Callaghan, Conor N.; McMurry, T. Brian H., Journal of Chemical Research, Miniprint, 1990, # 3, p. 601 - 619
  作者：O'Callaghan, Conor N.、McMurry, T. Brian H.

  DOI：——

  日期：——
• Electrochemical behaviour of an unsymmetrical 4-(o-nitrophenyl)-1,4-dihydropyridine in protic medium
  作者：J.Y. David、J.P. Hurvois、A. Tallec、L. Toupet

  DOI：10.1016/0040-4020(95)00057-f

  日期：1995.3

  The electrochemical behaviour of 3-cyano-5-methoxycarbonyl-2,6-dimethyl-4(o-nitrophenyl)-1,4-dihydropyridine and the corresponding N-methyl derivative have been investigated in hydroalcoolic medium. The 4 electron reduction leads to an amino-benzonaphtyridine N-oxide (cyclization from the reaction of the hydroxylamino group with the cyano substituent) when performed in acidic medium; in basic medium, the same reduction leads to a cyclic hydroxamic acid resulting from the condensation of the hydroxylamino group with the ester substituent. Anodic oxidations give the corresponding pyridine or pyridinium derivatives; subsequent reductions of the latter always lead to cyclic hydroxamic acids.