osajaxanthone | 1043-08-9

• 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: osajaxanthone
• 英文别名: Osajaxanthon；5,8-dihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one；5,8-Dihydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one
• CAS: 1043-08-9
• 化学式: C₁₈H₁₄O₅
• 分子量: 310.306
• InChiKey: AQJGDWRSGSISRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  osajaxanthone 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以100%的产率得到5,8-diacetoxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-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
• 作为产物：
  描述：

  7-hydroxy-1,3-dimethoxy-9H-xanthen-9-one 在 calcium hydroxide 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 osajaxanthone
  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.