3-acetamido-2,5-dimethoxyaniline | 856050-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-acetamido-2,5-dimethoxyaniline
• 英文别名: N-(3-amino-2,5-dimethoxyphenyl)acetamide；acetic acid-(3-amino-2,5-dimethoxy-anilide)；Essigsaeure-(3-amino-2,5-dimethoxy-anilid)
• CAS: 856050-03-8
• 化学式: C₁₀H₁₄N₂O₃
• 分子量: 210.233
• InChiKey: WVTPIOMTGPHLOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetamido-2,5-dimethoxyaniline 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 甲酸 、 PPA 、 硫酸 、 溶剂黄146 、 三乙胺 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 12.75h， 生成 7-cyano-5,8-dimethoxy-4-(2-nitrophenyl)quinolinone
  参考文献：
  名称：

  The Total Synthesis of Neoamphimedine

  摘要：

  Neoamphimedine, a pyridoacridine alkaloid from Xestospongia sp., is a potent antitumor agent both in vitro and in vivo. Neoamphimedine can efficiently induce topoisomerase II mediated catenation of plasmid DNA in vitro and is the only member of more than one hundred pyridoacridines thus far to have this mechanism of action. Herein we report the first total synthesis of neoamphimedine.

  DOI：

  10.1021/jo7017813
• 作为产物：
  描述：

  4-甲氧基-2-硝基酚 在 palladium on activated charcoal 硝酸 、 溶剂黄146 、 环己烯 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 24.33h， 生成 3-acetamido-2,5-dimethoxyaniline
  参考文献：
  名称：

  The Total Synthesis of Neoamphimedine

  摘要：

  Neoamphimedine, a pyridoacridine alkaloid from Xestospongia sp., is a potent antitumor agent both in vitro and in vivo. Neoamphimedine can efficiently induce topoisomerase II mediated catenation of plasmid DNA in vitro and is the only member of more than one hundred pyridoacridines thus far to have this mechanism of action. Herein we report the first total synthesis of neoamphimedine.

  DOI：

  10.1021/jo7017813

文献信息

• A Formal Synthesis of Lavendamycin Methyl Ester, Nitramarine, and Their Analogues: A Povarov Approach
  作者：Subburethinam Ramesh、Rajagopal Nagarajan

  DOI：10.1021/jo302389s

  日期：2013.1.18

  A convergent formal synthesis of lavendamycin methyl ester and synthesis of its analogues have been delineated through the Povarov approach. This protocol is also applied to the formal synthesis of nitramarine (3) in good yield.

  通过Povarov方法已经确定了拉文霉素甲酯的收敛形式合成及其类似物的合成。该方案也适用于以高收率的形式正式合成硝胺林（3）。
• Syntheses in the 5,8-Dihydroxyquinaldine Series
  作者：Alfred Burger、Gilmer T. Fitchett

  DOI：10.1021/ja01102a028

  日期：1953.3
• The Total Synthesis of Neoamphimedine
  作者：Daniel V. LaBarbera、Tim S. Bugni、Chris M. Ireland

  DOI：10.1021/jo7017813

  日期：2007.10.1

  Neoamphimedine, a pyridoacridine alkaloid from Xestospongia sp., is a potent antitumor agent both in vitro and in vivo. Neoamphimedine can efficiently induce topoisomerase II mediated catenation of plasmid DNA in vitro and is the only member of more than one hundred pyridoacridines thus far to have this mechanism of action. Herein we report the first total synthesis of neoamphimedine.