methyl N-(4-methoxy-3,5-dinitrophenyl)succinimidate | 210489-78-4

• 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: methyl N-(4-methoxy-3,5-dinitrophenyl)succinimidate
• 英文别名: Methyl 4-(4-methoxy-3,5-dinitroanilino)-4-oxobutanoate
• CAS: 210489-78-4
• 化学式: C₁₂H₁₃N₃O₈
• 分子量: 327.251
• InChiKey: GDDNLNSUCKXXQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl N-(4-methoxy-3,5-dinitrophenyl)succinimidate 在 硼烷四氢呋喃络合物 、 ammonium cerium(IV) nitrate 、 potassium tert-butylate 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 27.33h， 生成 methyl 1-formyl-6-methoxy-5,7-dinitro-3,4-dihydro-2H-quinoline-4-carboxylate
  参考文献：
  名称：

  Synthetic Routes to Pyrroloiminoquinone Alkaloids. A Direct Synthesis of Makaluvamine C

  摘要：

  Makaluvamine C is a pyrroloiminoquinone which has been isolated from marine sponges. This molecule has been synthesized in 13 steps from p-anisidine. The key steps in this synthesis include an intramolecular nucleophilic aromatic substitution mediated by potassium tert-butoxide, the selective reduction of a dinitro ester using catalytic hydrogenation, and the novel use of Fremy's salt to synthesize an iminoquinone from an amino phenol. The synthesis of makaluvamine C has been achieved from p-anisidine in 13.1% overall yield.

  DOI：

  10.1021/jo981547n
• 作为产物：
  描述：

  1-(4-甲氧基苯基)吡咯烷-2,5-二酮 在 硫酸 、 硝酸 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 生成 methyl N-(4-methoxy-3,5-dinitrophenyl)succinimidate
  参考文献：
  名称：

  用于合成吡咯亚氨基醌天然产物的关键三环中间体的制备

  摘要：

  吲哚 12 由对茴香胺分 7 个步骤制备。关键步骤是分子内亲核试剂芳香取代反应。

  DOI：

  10.1055/s-1998-867117

文献信息

• Preparation of a Key Tricyclic Intermediate for the Synthesis of Pyrroloiminoquinone Natural Products
  作者：George A. Kraus、Natesan Selvakumar

  DOI：10.1055/s-1998-867117

  日期：1998.8

  Indole 12 was prepared in seven steps from para-anisidine. The key step was an intramolecular nucleophile aromatic substitution reaction.

  吲哚 12 由对茴香胺分 7 个步骤制备。关键步骤是分子内亲核试剂芳香取代反应。
• Synthetic Routes to Pyrroloiminoquinone Alkaloids. A Direct Synthesis of Makaluvamine C
  作者：George A. Kraus、Natesan Selvakumar

  DOI：10.1021/jo981547n

  日期：1998.12.1

  Makaluvamine C is a pyrroloiminoquinone which has been isolated from marine sponges. This molecule has been synthesized in 13 steps from p-anisidine. The key steps in this synthesis include an intramolecular nucleophilic aromatic substitution mediated by potassium tert-butoxide, the selective reduction of a dinitro ester using catalytic hydrogenation, and the novel use of Fremy's salt to synthesize an iminoquinone from an amino phenol. The synthesis of makaluvamine C has been achieved from p-anisidine in 13.1% overall yield.