ethyl 3,9-dimethyl-7-(4-nitrophenyl)-6-oxo-6H-dibenzo[b,d]pyran-8-carboxylate | 1402930-69-1

• 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: ethyl 3,9-dimethyl-7-(4-nitrophenyl)-6-oxo-6H-dibenzo[b,d]pyran-8-carboxylate
• 英文别名: Ethyl 3,9-dimethyl-7-(4-nitrophenyl)-6-oxobenzo[c]chromene-8-carboxylate；ethyl 3,9-dimethyl-7-(4-nitrophenyl)-6-oxobenzo[c]chromene-8-carboxylate
• CAS: 1402930-69-1
• 化学式: C₂₄H₁₉NO₆
• 分子量: 417.418
• InChiKey: QJMIMRJDUKSMCD-UHFFFAOYSA-N

物化性质

• 熔点：
  205-208 °C
• 沸点：
  641.9±55.0 °C(predicted)
• 密度：
  1.313±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 3,9-dimethyl-7-(4-nitrophenyl)-6-oxo-7,8-dihydro-6Hdibenzo[b,d]pyran-8-carboxylate 在 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以75%的产率得到ethyl 3,9-dimethyl-7-(4-nitrophenyl)-6-oxo-6H-dibenzo[b,d]pyran-8-carboxylate
  参考文献：
  名称：

  Synthesis of 6H-Dibenzo[b,d]pyran-6-one Derivatives via Coumarin-Fused Cyclohexa-1,3-diene Intermediates

  摘要：

  In the presence of trifluoroacetic acid and methanesulfonic acid (MSA), a series of monohydric and polyhydric phenols readily undergo a domino Pechmann-dehydration reaction with various 4-hydroxy-6-oxocyclohexane-1,3-dicarboxylates to give 7,8-dihydro-6H-dibenzo[b,d]pyran-6-ones. Subsequent dehydrogenation of the 7,8-dihydro-6H-dibenzo[b,d]pyran-6-ones was performed expediently with DBU/BrCCl3 to give various 6H-dibenzo[b,d]pyran-6-one derivatives. This strategy has the advantages of inexpensive and easily available raw materials, metal-free procedure, mild reaction conditions, good compatibility with various functional groups, and satisfactory yields.

  DOI：

  10.1055/s-0031-1289810

文献信息

• Synthesis of 6H-Dibenzo[b,d]pyran-6-one Derivatives via Coumarin-Fused Cyclohexa-1,3-diene Intermediates
  作者：Zhi-Zhen Huang、Chao-Yue Chen、Yong-Sheng Zhao、Chang-Bing Xiang

  DOI：10.1055/s-0031-1289810

  日期：2012.8

  In the presence of trifluoroacetic acid and methanesulfonic acid (MSA), a series of monohydric and polyhydric phenols readily undergo a domino Pechmann-dehydration reaction with various 4-hydroxy-6-oxocyclohexane-1,3-dicarboxylates to give 7,8-dihydro-6H-dibenzo[b,d]pyran-6-ones. Subsequent dehydrogenation of the 7,8-dihydro-6H-dibenzo[b,d]pyran-6-ones was performed expediently with DBU/BrCCl3 to give various 6H-dibenzo[b,d]pyran-6-one derivatives. This strategy has the advantages of inexpensive and easily available raw materials, metal-free procedure, mild reaction conditions, good compatibility with various functional groups, and satisfactory yields.