1-acetoxy-3-dibromomethyl-9H-xanthen-9-one | 1256668-30-0

• 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: 1-acetoxy-3-dibromomethyl-9H-xanthen-9-one
• CAS: 1256668-30-0
• 化学式: C₁₆H₁₀Br₂O₄
• 分子量: 426.061
• InChiKey: WUDDWOSGWWJZBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  56.51
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-acetoxy-3-methyl-9H-xanthen-9-one 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 16.0h， 生成 1-acetoxy-3-bromomethyl-9H-xanthen-9-one 、 1-acetoxy-3-dibromomethyl-9H-xanthen-9-one
  参考文献：
  名称：

  Synthesis of Hexacyclic Parnafungin A and C Models

  摘要：

  A convergent, practical route to unstable hexacyclic parnafungin A and C models has been developed. Two iodoxanthones were prepared in four or five steps (33-50% overall yield). Suzuki-Miyaura coupling of the iodoxanthones with excess readily available 3-carbomethoxy-2-nitrophenyl pinacol boronate afforded the hindered highly functionalized 2-arylxanthones (53-58%) in the first key step. In the second key step, zinc reduction gave benzisoxazolinones that were treated with MsCl and then base to generate the unstable hexacyclic parnafungin A (13% overall yield for 8 steps) and C (8% overall yield for 9 steps) models. Analogously to the parnafungins, hexacyclic parnafungin C model decomposes to a phenanthridine with a half-life of 2 d in CDCI3.

  DOI：

  10.1021/jo101826p