2-(7,8-dihydronaphtho[2,3-d][1,3]dioxol-6-yl)-4-hydroxy-5-methoxybenzaldehyde O-methyl oxime | 1581303-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(7,8-dihydronaphtho[2,3-d][1,3]dioxol-6-yl)-4-hydroxy-5-methoxybenzaldehyde O-methyl oxime
• CAS: 1581303-17-4
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: JUPYFOKPLUVSEE-UHFFFAOYSA-N

物化性质

• 沸点：
  537.3±60.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.51
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(7,8-dihydronaphtho[2,3-d][1,3]dioxol-6-yl)-4-hydroxy-5-methoxybenzaldehyde O-methyl oxime 在 palladium 10% on activated carbon 作用下， 以 邻二氯苯 为溶剂， 反应 24.5h， 生成 dihydroisoterihanine
  参考文献：
  名称：

  Total Synthesis of the Benzo[c]phenanthridine Alkaloids, Terihanine and Isoterihanine, and Their Antitumor Activity

  摘要：

  A new total synthesis of terihanine (2a) and isoterihanine (2b) was established by our new bond formation between the C4b and N5 positions of the benzo[c]phenanthridine ring based on a microwave-assisted thermal electrocyclic reaction of 2-cycloalkenylbenzaldoxime as an aza 6 pi-electron system. In addition, the antitumor activity of these synthesized compounds, including nitidine and nornitidine was evaluated in HCT-116 cells.

  DOI：

  10.3987/com-13-s(s)16
• 作为产物：
  描述：

  4-乙酰氧基-2-溴-5-甲氧基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-(7,8-dihydronaphtho[2,3-d][1,3]dioxol-6-yl)-4-hydroxy-5-methoxybenzaldehyde O-methyl oxime
  参考文献：
  名称：

  Total Synthesis of the Benzo[c]phenanthridine Alkaloids, Terihanine and Isoterihanine, and Their Antitumor Activity

  摘要：

  A new total synthesis of terihanine (2a) and isoterihanine (2b) was established by our new bond formation between the C4b and N5 positions of the benzo[c]phenanthridine ring based on a microwave-assisted thermal electrocyclic reaction of 2-cycloalkenylbenzaldoxime as an aza 6 pi-electron system. In addition, the antitumor activity of these synthesized compounds, including nitidine and nornitidine was evaluated in HCT-116 cells.

  DOI：

  10.3987/com-13-s(s)16