(E)-4-(6,7-dimethoxy-8-(4-hydroxyphenyl)-1-nitromethylisoquinolin-2(1H)-yl)-3-buten-2-one | 1242068-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-4-(6,7-dimethoxy-8-(4-hydroxyphenyl)-1-nitromethylisoquinolin-2(1H)-yl)-3-buten-2-one
• 英文别名: (E)-4-[8-(4-hydroxyphenyl)-6,7-dimethoxy-1-(nitromethyl)-1H-isoquinolin-2-yl]but-3-en-2-one
• CAS: 1242068-66-1
• 化学式: C₂₂H₂₂N₂O₆
• 分子量: 410.426
• InChiKey: GXOHFFYDPDOZAO-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (E)-4-(6,7-dimethoxy-1-nitromethyl-8-[4-(triisopropylsiloxy)phenyl]isoquinolin-2(1H)-yl)-3-buten-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以98%的产率得到(E)-4-(6,7-dimethoxy-8-(4-hydroxyphenyl)-1-nitromethylisoquinolin-2(1H)-yl)-3-buten-2-one
  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.