4-hydroxy-3-methoxy-2,β-dinitrostyrene | 6291-50-5

• 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: 4-hydroxy-3-methoxy-2,β-dinitrostyrene
• 英文别名: GRI 402297；(E)-2-methoxy-3-nitro-4-(2-nitrovinyl)phenol；2-methoxy-3-nitro-4-(2-nitroethenyl)phenol
• CAS: 6291-50-5
• 化学式: C₉H₈N₂O₆
• 分子量: 240.172
• InChiKey: ZAUXRJBGUWQKHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-methoxy-2,β-dinitrostyrene 在 palladium 10% on activated carbon 、 甲酸铵 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 15.33h， 以38%的产率得到6-hydroxy-7-methoxyindole
  参考文献：
  名称：

  First Total Synthesis of 9-Hydroxy-8H-pyrano[3,2-f]indol-2-one

  摘要：

  A simple and efficient approach to synthesize a novel pyrrolocoumarin 9‐hydroxy‐8H‐pyrano[3,2‐f]indol‐2‐one (7) has been described. Starting from vanillin, the key intermediate 7‐methoxy‐1H‐indol‐6‐yl propiolate (6) was synthesized in six steps. Then, the target compound was obtained by forming pyrone‐ring and demethylation simultaneously in one step. A plausible mechanism invoking PtCl4 catalyzed one‐step reaction of cyclization and demethylation was also presented.

  DOI：

  10.1002/jhet.2251
• 作为产物：
  描述：

  4-甲酰基-2-甲氧基-3-硝基乙酸苯酯 在 ammonium acetate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.5h， 生成 4-hydroxy-3-methoxy-2,β-dinitrostyrene
  参考文献：
  名称：

  First Total Synthesis of 9-Hydroxy-8H-pyrano[3,2-f]indol-2-one

  摘要：

  A simple and efficient approach to synthesize a novel pyrrolocoumarin 9‐hydroxy‐8H‐pyrano[3,2‐f]indol‐2‐one (7) has been described. Starting from vanillin, the key intermediate 7‐methoxy‐1H‐indol‐6‐yl propiolate (6) was synthesized in six steps. Then, the target compound was obtained by forming pyrone‐ring and demethylation simultaneously in one step. A plausible mechanism invoking PtCl4 catalyzed one‐step reaction of cyclization and demethylation was also presented.

  DOI：

  10.1002/jhet.2251

文献信息

• First Total Synthesis of 9-Hydroxy-8<i>H</i>-pyrano[3,2-<i>f</i>]indol-2-one
  作者：Tao Wang、Cheng Wang、Jie Zhang、Huaizhen He

  DOI：10.1002/jhet.2251

  日期：2015.9

  A simple and efficient approach to synthesize a novel pyrrolocoumarin 9‐hydroxy‐8H‐pyrano[3,2‐f]indol‐2‐one (7) has been described. Starting from vanillin, the key intermediate 7‐methoxy‐1H‐indol‐6‐yl propiolate (6) was synthesized in six steps. Then, the target compound was obtained by forming pyrone‐ring and demethylation simultaneously in one step. A plausible mechanism invoking PtCl4 catalyzed one‐step reaction of cyclization and demethylation was also presented.