6,9-dihydroxy-3-methyl-3-(4-methylpent-3-enyl)-3H,7H-pyrano[2,3-c]xanthen-7-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6,9-dihydroxy-3-methyl-3-(4-methylpent-3-enyl)-3H,7H-pyrano[2,3-c]xanthen-7-one
• 英文别名: 6,9-Dihydroxy-3-methyl-3-(4-methylpent-3-enyl)pyrano[2,3-c]xanthen-7-one
• 化学式: C₂₃H₂₂O₅
• 分子量: 378.425
• InChiKey: CNGZKWUBKJBFLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3,7-三羟基-9H-氧杂蒽-9-酮 、 柠檬醛 反应 6.0h， 以80%的产率得到6,9-dihydroxy-3-methyl-3-(4-methylpent-3-enyl)-3H,7H-pyrano[2,3-c]xanthen-7-one
  参考文献：
  名称：

  Facile Synthesis of 1,3,7-Trihydroxyxanthone and Its Regioselective Coupling Reactions with Prenal:  Simple and Efficient Access to Osajaxanthone and Nigrolineaxanthone F

  摘要：

  A facile five-step synthesis of naturally occurring 1,3,7-trihydroxyxanthone has been described starting from 1,3,5-trimethoxybenzene via NBS-induced nuclear bromination, lithiation followed by an in situ benzoylation with methyl 2,5-dibenzyloxybenzoate, selective deprotection of the two benzyl groups, base-catalyzed intramolecular cyclization, and demethylations pathway with 62% overall yield. The regioselective coupling reactions of 1,3,7-trihydroxyxanthone with prenal in the presence of calcium hydroxide at room temperature and under thermal conditions at 140-150 degrees C have been demonstrated to exclusively obtain the natural products osajaxanthone in 75% yield and nigrolineaxanthone F in 98% yield, respectively.

  DOI：

  10.1021/jo0606655

文献信息

• Facile Synthesis of 1,3,7-Trihydroxyxanthone and Its Regioselective Coupling Reactions with Prenal:  Simple and Efficient Access to Osajaxanthone and Nigrolineaxanthone F
  作者：Mukulesh Mondal、Vedavati G. Puranik、Narshinha P. Argade

  DOI：10.1021/jo0606655

  日期：2006.6.1

  A facile five-step synthesis of naturally occurring 1,3,7-trihydroxyxanthone has been described starting from 1,3,5-trimethoxybenzene via NBS-induced nuclear bromination, lithiation followed by an in situ benzoylation with methyl 2,5-dibenzyloxybenzoate, selective deprotection of the two benzyl groups, base-catalyzed intramolecular cyclization, and demethylations pathway with 62% overall yield. The regioselective coupling reactions of 1,3,7-trihydroxyxanthone with prenal in the presence of calcium hydroxide at room temperature and under thermal conditions at 140-150 degrees C have been demonstrated to exclusively obtain the natural products osajaxanthone in 75% yield and nigrolineaxanthone F in 98% yield, respectively.