ethyl 1,3-dihydroxy-9-methyl-6-oxo-7-phenyl-7,8-dihydro-6H-dibenzo[b,d]pyran-8-carboxylate | 1402930-66-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: ethyl 1,3-dihydroxy-9-methyl-6-oxo-7-phenyl-7,8-dihydro-6H-dibenzo[b,d]pyran-8-carboxylate
• CAS: 1402930-66-8
• 化学式: C₂₃H₂₀O₆
• 分子量: 392.408
• InChiKey: YKXCQODZXKBNQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  96.97
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 1,3-dihydroxy-9-methyl-6-oxo-7-phenyl-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52%的产率得到ethyl 1,3-dihydroxy-9-methyl-6-oxo-7-phenyl-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
• 作为产物：
  描述：

  间苯三酚 、 4-羟基-4-甲基-6-氧代-2-苯基-1,3-环已二酸二乙酯 在 甲烷磺酸 、 三氟乙酸 作用下， 反应 24.0h， 以63%的产率得到ethyl 1,3-dihydroxy-9-methyl-6-oxo-7-phenyl-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