1-methyl-6-methoxy-3-diazoquinoline-2,4-dione | 223668-12-0

• 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: 1-methyl-6-methoxy-3-diazoquinoline-2,4-dione
• 英文别名: 3-Diazonio-6-methoxy-1-methyl-4-oxoquinolin-2-olate
• CAS: 223668-12-0
• 化学式: C₁₁H₉N₃O₃
• 分子量: 231.211
• InChiKey: GIUCKPJIWBPTFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-6-methoxy-3-diazoquinoline-2,4-dione 在 dirhodium tetraacetate 作用下， 以 乙腈 为溶剂， 以87%的产率得到1,3-二氢-5-甲氧基-1-甲基-2H-吲哚-2-酮
  参考文献：
  名称：

  Efficient synthesis of oxindoles by thermal and rhodium(II)-catalyzed Wolff rearrangement

  摘要：

  An efficient synthesis of oxindoles is achieved from a thermal and rhodium(II)-catalyzed Wolff rearrangement of diazoquinolinediones in moderate yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01714-1
• 作为产物：
  描述：

  4-羟基-6-甲氧基-1-甲基-2(1H)-喹啉酮 在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以73%的产率得到1-methyl-6-methoxy-3-diazoquinoline-2,4-dione
  参考文献：
  名称：

  Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones

  摘要：

  As an entry to furoquinoline structures of natural origin, the rhodium-mediated dipolar cycloaddition of diazoquinolinediones with alkenes and alkynes has been examined. Because of the unsymmetrical nature of the diazo compounds, both linear and angular furoquinoline products are possible. For the most part, a mixture of regioisomers is generated in moderate to good yields, though in a few cases dominant products are obtained in high yields. The products can be further converted to naturally occurring alkaloids such as isodictamnine. A novel observation in this work is that catalytic quantities of acid enhance the yield and regiochemical control in the cycloaddition.

  DOI：

  10.1021/jo982503h

文献信息

• Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones
  作者：Michael C. Pirrung、Florian Blume

  DOI：10.1021/jo982503h

  日期：1999.5.1

  As an entry to furoquinoline structures of natural origin, the rhodium-mediated dipolar cycloaddition of diazoquinolinediones with alkenes and alkynes has been examined. Because of the unsymmetrical nature of the diazo compounds, both linear and angular furoquinoline products are possible. For the most part, a mixture of regioisomers is generated in moderate to good yields, though in a few cases dominant products are obtained in high yields. The products can be further converted to naturally occurring alkaloids such as isodictamnine. A novel observation in this work is that catalytic quantities of acid enhance the yield and regiochemical control in the cycloaddition.
• Efficient synthesis of oxindoles by thermal and rhodium(II)-catalyzed Wolff rearrangement
  作者：Yong Rok Lee、Jung Yup Suk、Byung So Kim

  DOI：10.1016/s0040-4039(99)01714-1

  日期：1999.11

  An efficient synthesis of oxindoles is achieved from a thermal and rhodium(II)-catalyzed Wolff rearrangement of diazoquinolinediones in moderate yields. (C) 1999 Elsevier Science Ltd. All rights reserved.