nigrolineaxanthone F | 26486-88-4

• 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: nigrolineaxanthone F
• 英文别名: 6,9-dihydroxy-3,3-dimethylpyrano[2,3-c]xanthen-7-one
• CAS: 26486-88-4
• 化学式: C₁₈H₁₄O₅
• 分子量: 310.306
• InChiKey: TZPXKEYIVMJZOB-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：

  nigrolineaxanthone F 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以100%的产率得到6,9-diacetoxy-3,3-dimethyl-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
• 作为产物：
  描述：

  7-hydroxy-1,3-dimethoxy-9H-xanthen-9-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 nigrolineaxanthone F
  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

• [EN] MOLECULAR DESIGN OF NEW ANTIBIOTICS AND ANTIBIOTIC ADJUVANTS AGAINST MCR STRAINS<br/>[FR] CONCEPTION MOLÉCULAIRE DE NOUVEAUX ANTIBIOTIQUES ET ADJUVANTS D'ANTIBIOTIQUES CONTRE LES SOUCHES MCR
  申请人：SINGAPORE HEALTH SERV PTE LTD

  公开号：WO2020236084A1

  公开（公告）日：2020-11-26

  The present invention relates to a compound comprising a hydrophobic moiety, a linker and N-containing moiety. The present invention also relates to the method of synthesizing the compound and the use of the compound as an antibiotic or an adjuvant for an antibiotic.

  本发明涉及一种包含疏水基团、连接剂和含氮基团的化合物。本发明还涉及合成该化合物的方法以及将该化合物用作抗生素或抗生素辅助剂的用途。
• 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.