3-(6-methyl-2-oxo-2H-chromen-4-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl acetate | 879501-47-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(6-methyl-2-oxo-2H-chromen-4-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl acetate
• 英文别名: [3-(6-methyl-2-oxochromen-4-yl)-2-oxo-5H-pyrano[3,2-c]chromen-5-yl] acetate
• CAS: 879501-47-0
• 化学式: C₂₄H₁₆O₇
• 分子量: 416.387
• InChiKey: LVKRQCOYGFMKLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  244-247 °C
• 沸点：
  683.6±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(6-methyl-2-oxo-2H-chromen-4-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl acetate 在 溶剂黄146 作用下， 反应 0.5h， 生成 5-hydroxy-3-(6-methyl-2-oxo-2H-chromen-4-yl)pyrano[2,3-b]chromen-2(10aH)-one
  参考文献：
  名称：

  Convenient synthesis and unusual reactivity of 2-oxo-2H,5H-pyrano[3,2-c]chromenes

  摘要：

  The reaction of 4-oxo-4H-chromen-3-carbaldehydes with coumarin-4-acetic acids under the Perkin conditions follows an interesting pathway that involves aldol reaction and subsequent intramolecular lactonization to afford 2-oxo-2H,5H-pyrano[3,2-c]chromene skeleton. In contrast to chromone-3-carbaldehydes, the same reaction with chromone-2-carbaldehydes yielded only the aldol condensation product. The reaction was performed under thermal and microwave conditions. The reactivity of 2-oxo2H,5H-pyrano[3,2-c]chromenes in water, alcohol and acetic acid was described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.032
• 作为产物：
  描述：

  6-methylcoumarin-4-acetic acid 、 乙酸酐 、 色酮-3-甲醛 在 potassium acetate 作用下， 反应 0.17h， 以75%的产率得到3-(6-methyl-2-oxo-2H-chromen-4-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl acetate
  参考文献：
  名称：

  Convenient synthesis and unusual reactivity of 2-oxo-2H,5H-pyrano[3,2-c]chromenes

  摘要：

  The reaction of 4-oxo-4H-chromen-3-carbaldehydes with coumarin-4-acetic acids under the Perkin conditions follows an interesting pathway that involves aldol reaction and subsequent intramolecular lactonization to afford 2-oxo-2H,5H-pyrano[3,2-c]chromene skeleton. In contrast to chromone-3-carbaldehydes, the same reaction with chromone-2-carbaldehydes yielded only the aldol condensation product. The reaction was performed under thermal and microwave conditions. The reactivity of 2-oxo2H,5H-pyrano[3,2-c]chromenes in water, alcohol and acetic acid was described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.032

文献信息

• Convenient synthesis and unusual reactivity of 2-oxo-2H,5H-pyrano[3,2-c]chromenes
  作者：Margita Lácová、Henrieta Stankovičová、Andrej Boháč、Bibiána Kotzianová

  DOI：10.1016/j.tet.2008.07.032

  日期：2008.9

  The reaction of 4-oxo-4H-chromen-3-carbaldehydes with coumarin-4-acetic acids under the Perkin conditions follows an interesting pathway that involves aldol reaction and subsequent intramolecular lactonization to afford 2-oxo-2H,5H-pyrano[3,2-c]chromene skeleton. In contrast to chromone-3-carbaldehydes, the same reaction with chromone-2-carbaldehydes yielded only the aldol condensation product. The reaction was performed under thermal and microwave conditions. The reactivity of 2-oxo2H,5H-pyrano[3,2-c]chromenes in water, alcohol and acetic acid was described. (C) 2008 Elsevier Ltd. All rights reserved.