7,8-dimethoxy-2-nitrospiro(3-azaacenaphthylene-1(2H)-4'-cyclohexan)-2',5'-dienone | 1262392-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 7,8-dimethoxy-2-nitrospiro(3-azaacenaphthylene-1(2H)-4'-cyclohexan)-2',5'-dienone
• 英文别名: 10,11-Dimethoxy-3-nitrospiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaene-2,4'-cyclohexa-2,5-diene]-1'-one
• CAS: 1262392-78-8
• 化学式: C₁₈H₁₄N₂O₅
• 分子量: 338.32
• InChiKey: FNRFNLXNQVVWDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  94.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,8-dimethoxy-2-nitrospiro(3-azaacenaphthylene-1(2H)-4'-cyclohexan)-2',5'-dienone 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到pareitropone
  参考文献：
  名称：

  Total Synthesis of Pareitropone via Radical Anion Coupling

  摘要：

  A concise (9-step) synthesis of the tropoloisoquinoline alkaloid pareitropone has been achieved starting from 2-bromoisovanillin. The key step features oxidative cyclization of a readily available phenolic nitronate for the convenient construction of the fused tropone ring. This work underscores the synthetic utility of intramolecular oxidative coupling reactions of phenolic nitronates.

  DOI：

  10.1021/ol1017849
• 作为产物：
  描述：

  (E)-4-(6,7-dimethoxy-8-(4-hydroxyphenyl)-1-nitromethylisoquinolin-2(1H)-yl)-3-buten-2-one 在 potassium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 以76%的产率得到7,8-dimethoxy-2-nitrospiro(3-azaacenaphthylene-1(2H)-4'-cyclohexan)-2',5'-dienone
  参考文献：
  名称：

  Total Synthesis of Pareitropone via Radical Anion Coupling

  摘要：

  A concise (9-step) synthesis of the tropoloisoquinoline alkaloid pareitropone has been achieved starting from 2-bromoisovanillin. The key step features oxidative cyclization of a readily available phenolic nitronate for the convenient construction of the fused tropone ring. This work underscores the synthetic utility of intramolecular oxidative coupling reactions of phenolic nitronates.

  DOI：

  10.1021/ol1017849

文献信息

• Total Synthesis of Pareitropone via Radical Anion Coupling
  作者：Suk-Koo Hong、Hyeonjeong Kim、Youngran Seo、Sang Hyup Lee、Jin Kun Cha、Young Gyu Kim

  DOI：10.1021/ol1017849

  日期：2010.9.3

  A concise (9-step) synthesis of the tropoloisoquinoline alkaloid pareitropone has been achieved starting from 2-bromoisovanillin. The key step features oxidative cyclization of a readily available phenolic nitronate for the convenient construction of the fused tropone ring. This work underscores the synthetic utility of intramolecular oxidative coupling reactions of phenolic nitronates.