Methyl 3-(1-acetyloxy-3-methyl-9-oxoxanthen-2-yl)-2-nitrobenzoate | 1256668-26-4

• 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: Methyl 3-(1-acetyloxy-3-methyl-9-oxoxanthen-2-yl)-2-nitrobenzoate
• CAS: 1256668-26-4
• 化学式: C₂₄H₁₇NO₈
• 分子量: 447.401
• InChiKey: YZRUEWZRQYOUIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 3-(1-acetyloxy-3-methyl-9-oxoxanthen-2-yl)-2-nitrobenzoate 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， 以60%的产率得到Methyl 3-[1-acetyloxy-3-(bromomethyl)-9-oxoxanthen-2-yl]-2-nitrobenzoate
  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：

  methyl 2-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 、 1-Hydroxy-2-iodo-3-methylxanthen-9-one 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 、 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate tribasic 、 palladium diacetate 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以60%的产率得到Methyl 3-(1-acetyloxy-3-methyl-9-oxoxanthen-2-yl)-2-nitrobenzoate
  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