4-methyl-8-[(2-morpholin-4-ylethylamino)methylene]-2,7-dioxo-7,8-dihydro-2H-benzo[h]chromene-10-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 4-methyl-8-[(2-morpholin-4-ylethylamino)methylene]-2,7-dioxo-7,8-dihydro-2H-benzo[h]chromene-10-carbaldehyde
• 英文别名: (8Z)-4-methyl-8-[(2-morpholin-4-ylethylamino)methylidene]-2,7-dioxobenzo[h]chromene-10-carbaldehyde
• 化学式: C₂₂H₂₂N₂O₅
• 分子量: 394.427
• InChiKey: BMBDKXWZKFXIBJ-QINSGFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  88.85
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  4-甲基-7-羟基-8-硝基香豆素 在 硫酸 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 0.02h， 生成 4-methyl-8-[(2-morpholin-4-ylethylamino)methylene]-2,7-dioxo-7,8-dihydro-2H-benzo[h]chromene-10-carbaldehyde
  参考文献：
  名称：

  Highly efficient and regioselective synthesis of keto-enamine Schiff bases of 7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromene-8,10-dicarbaldehyde and 1-hydroxynaphthalene-2,4-dicarbaldehyde

  摘要：

  A series of novel Schiff bases has been synthesized by reacting 7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromene-8,10-dicarbaldehyde 3 and 1-hydroxynaphthalene-2,4-dicarbaldehyde 8 with several primary alkylamines in ethyl alcohol at room temperature within 1-2 min. Schiff bases 4a-i and 9 were formed regioselectively by condensation with only one aldehyde, which is in chelation with a hydroxyl group. Extensive 2D NMR spectroscopic studies revealed that all the compounds 4a-i and 9 exist in the keto-enamine tautomeric form at room temperature. The high reactivity, regioselectivity and stable keto-enamine tautomeric form are due to the presence of an electron-withdrawing aldehyde group. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.044

文献信息

• Highly efficient and regioselective synthesis of keto-enamine Schiff bases of 7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromene-8,10-dicarbaldehyde and 1-hydroxynaphthalene-2,4-dicarbaldehyde
  作者：Koneni V. Sashidhara、Jammikuntla N. Rosaiah、Tadigoppula Narender

  DOI：10.1016/j.tetlet.2007.01.044

  日期：2007.3

  A series of novel Schiff bases has been synthesized by reacting 7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromene-8,10-dicarbaldehyde 3 and 1-hydroxynaphthalene-2,4-dicarbaldehyde 8 with several primary alkylamines in ethyl alcohol at room temperature within 1-2 min. Schiff bases 4a-i and 9 were formed regioselectively by condensation with only one aldehyde, which is in chelation with a hydroxyl group. Extensive 2D NMR spectroscopic studies revealed that all the compounds 4a-i and 9 exist in the keto-enamine tautomeric form at room temperature. The high reactivity, regioselectivity and stable keto-enamine tautomeric form are due to the presence of an electron-withdrawing aldehyde group. (c) 2007 Elsevier Ltd. All rights reserved.