4-(3-cyano-7,7-dimethyl-2,5-dioxo-5,6,7,8-tetrahydro-2Hquinolin-1-ylamino)-benzoic acid methyl ester | 1296687-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(3-cyano-7,7-dimethyl-2,5-dioxo-5,6,7,8-tetrahydro-2Hquinolin-1-ylamino)-benzoic acid methyl ester
• 英文别名: Methyl 4-[(3-cyano-7,7-dimethyl-2,5-dioxo-6,8-dihydroquinolin-1-yl)amino]benzoate；methyl 4-[(3-cyano-7,7-dimethyl-2,5-dioxo-6,8-dihydroquinolin-1-yl)amino]benzoate
• CAS: 1296687-78-9
• 化学式: C₂₀H₁₉N₃O₄
• 分子量: 365.389
• InChiKey: STBVJLVXCCPUOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  以 水 、 异丙醇 为溶剂， 反应 0.08h， 以388 mg的产率得到4-(3-cyano-7,7-dimethyl-2,5-dioxo-5,6,7,8-tetrahydro-2Hquinolin-1-ylamino)-benzoic acid methyl ester
  参考文献：
  名称：

  Pathways for cyclizations of hydrazine-derived 2-(2-cyanovinyl)-3-oxo-cyclohex-1-ene enolates

  摘要：

  The introduction of a hydrazine functionality into 2-(2-cyanovinyl)-3-oxo-cyclohex-1-ene enolates results in their spontaneous cyclizations with participation of the hydrazine moiety. Depending on the reaction conditions used, the hydrazine-derived enolates are transformed into derivatives of 1-arylpyridine-2-one-3-carbonitriles or pyrazoloquinolinones in a one-pot synthesis. They also react with anilines to give the corresponding N1-substituted pyridine-2-one-3-carboxamides. Product characterization was performed by means of spectroscopic and X-ray diffraction studies. In addition, for structure elucidation purposes, a counter synthesis of 1-arylaminopyridine-2-one-3-carboxamide was also carried out. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.052

文献信息

• Pathways for cyclizations of hydrazine-derived 2-(2-cyanovinyl)-3-oxo-cyclohex-1-ene enolates
  作者：Sergey A. Yermolayev、Nickolay Yu. Gorobets、Oleg V. Shishkin、Svetlana V. Shishkina、Nicholas E. Leadbeater

  DOI：10.1016/j.tet.2011.02.052

  日期：2011.4

  The introduction of a hydrazine functionality into 2-(2-cyanovinyl)-3-oxo-cyclohex-1-ene enolates results in their spontaneous cyclizations with participation of the hydrazine moiety. Depending on the reaction conditions used, the hydrazine-derived enolates are transformed into derivatives of 1-arylpyridine-2-one-3-carbonitriles or pyrazoloquinolinones in a one-pot synthesis. They also react with anilines to give the corresponding N1-substituted pyridine-2-one-3-carboxamides. Product characterization was performed by means of spectroscopic and X-ray diffraction studies. In addition, for structure elucidation purposes, a counter synthesis of 1-arylaminopyridine-2-one-3-carboxamide was also carried out. (C) 2011 Elsevier Ltd. All rights reserved.