4,7-dihydro-15-methoxy-[1]benzopyrano[2,3-j]isoxazolo[4,3,2-de]phenanthridine-4,14-dione | 1256668-39-9

• 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: 4,7-dihydro-15-methoxy-[1]benzopyrano[2,3-j]isoxazolo[4,3,2-de]phenanthridine-4,14-dione
• 英文别名: 3-Methoxy-12,18-dioxa-17-azahexacyclo[15.6.1.02,15.04,13.06,11.020,24]tetracosa-1(23),2,4(13),6,8,10,14,20(24),21-nonaene-5,19-dione
• CAS: 1256668-39-9
• 化学式: C₂₂H₁₃NO₅
• 分子量: 371.349
• InChiKey: RARKTLGBLKZOET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,7-dihydro-15-methoxy-[1]benzopyrano[2,3-j]isoxazolo[4,3,2-de]phenanthridine-4,14-dione 以 氘代氯仿 为溶剂， 生成 14-hydroxy-13-oxo-13H-[1]benzopyrano[2,3-j]phenanthridine-4-carboxylic acid
  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：

  在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以5 mg的产率得到4,7-dihydro-15-methoxy-[1]benzopyrano[2,3-j]isoxazolo[4,3,2-de]phenanthridine-4,14-dione
  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

文献信息

• Synthesis of Hexacyclic Parnafungin A and C Models
  作者：Quan Zhou、Barry B. Snider

  DOI：10.1021/jo101826p

  日期：2010.12.3

  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.