7-BOC-amino-8-methoxy-5-methyl-1,3,4,5-tetrahydropyrrolo<4,3,2-de>quinoline | 219660-83-0

• 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: 7-BOC-amino-8-methoxy-5-methyl-1,3,4,5-tetrahydropyrrolo<4,3,2-de>quinoline
• 英文别名: tert-butyl N-(11-methoxy-7-methyl-2,7-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraen-10-yl)carbamate
• CAS: 219660-83-0
• 化学式: C₁₇H₂₃N₃O₃
• 分子量: 317.388
• InChiKey: WGENGQDDDJLWJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-BOC-amino-8-methoxy-5-methyl-1,3,4,5-tetrahydropyrrolo<4,3,2-de>quinoline 在 potassium nitrososulfonate 、 6-(对甲苯氨基)-2-萘磺酰氯 、 sodium iodide 作用下， 生成 makaluvamine C
  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 palladium on activated charcoal 硼烷四氢呋喃络合物 、 氢气 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 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

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.