ethyl 3,4-dihydroxy-9-methyl-7-(4-nitrophenyl)-6-oxo-7,8-dihydro-6H-dibenzo[b,d]pyran-8-carboxylate | 1402930-65-7

• 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 3,4-dihydroxy-9-methyl-7-(4-nitrophenyl)-6-oxo-7,8-dihydro-6H-dibenzo[b,d]pyran-8-carboxylate
• CAS: 1402930-65-7
• 化学式: C₂₃H₁₉NO₈
• 分子量: 437.406
• InChiKey: LLZVKHJBUHMXGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  140.11
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 3,4-dihydroxy-9-methyl-7-(4-nitrophenyl)-6-oxo-7,8-dihydro-6H-dibenzo[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54%的产率得到ethyl 3,4-dihydroxy-9-methyl-7-(4-nitrophenyl)-6-oxo-6Hdibenzo[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
• 作为产物：
  描述：

  5-hydroxy-5-methyl-3-(4-nitrophenyl)cyclohexanone-2,4-dicarboxylic acid diethyl ester 、 邻苯三酚 在 甲烷磺酸 、 三氟乙酸 作用下， 反应 24.0h， 以79%的产率得到ethyl 3,4-dihydroxy-9-methyl-7-(4-nitrophenyl)-6-oxo-7,8-dihydro-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