methyl N-methyl-1,2,3,4-tetrahydro-6-methoxy-5,7-dinitroquinoline-4-carboxylate | 219660-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl N-methyl-1,2,3,4-tetrahydro-6-methoxy-5,7-dinitroquinoline-4-carboxylate
• 英文别名: methyl 6-methoxy-1-methyl-5,7-dinitro-3,4-dihydro-2H-quinoline-4-carboxylate
• CAS: 219660-78-3
• 化学式: C₁₃H₁₅N₃O₇
• 分子量: 325.278
• InChiKey: GCZKNRSKACVRPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl N-methyl-1,2,3,4-tetrahydro-6-methoxy-5,7-dinitroquinoline-4-carboxylate 在 palladium on activated charcoal 氢气 、 二异丁基氢化铝 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 75.5h， 生成 7-BOC-amino-8-methoxy-5-methyl-1,3,4,5-tetrahydropyrrolo<4,3,2-de>quinoline
  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：

  methyl 1-formyl-6-methoxy-5,7-dinitro-3,4-dihydro-2H-quinoline-4-carboxylate 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到methyl N-methyl-1,2,3,4-tetrahydro-6-methoxy-5,7-dinitroquinoline-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

文献信息

• 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.