1-hydroxy-3-hydroxymethyl-2-iodo-9H-xanthen-9-one | 1256668-31-1

• 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-hydroxy-3-hydroxymethyl-2-iodo-9H-xanthen-9-one
• 英文别名: 1-Hydroxy-3-(hydroxymethyl)-2-iodoxanthen-9-one
• CAS: 1256668-31-1
• 化学式: C₁₄H₉IO₄
• 分子量: 368.128
• InChiKey: DCBPRGMLODWHRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 、 1-hydroxy-3-hydroxymethyl-2-iodo-9H-xanthen-9-one 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate tribasic 、 palladium diacetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以58%的产率得到1-hydroxy-3-hydroxymethyl-2-(2-nitro-3-methoxycarbonylphenyl)-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
• 作为产物：
  描述：

  1-hydroxy-3-hydroxymethyl-9H-xanthen-9-one 在 碘 、 高碘酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 40.0h， 生成 1-hydroxy-3-hydroxymethyl-2-iodo-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