ethyl 8,9-dimethoxy-3,6-dioxo-5,6-dihydro-3H-pyran<2,3-c>isoquinoline-2-carboxylate | 141990-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: ethyl 8,9-dimethoxy-3,6-dioxo-5,6-dihydro-3H-pyran<2,3-c>isoquinoline-2-carboxylate
• 英文别名: ethyl 8,9-dimethoxy-3,6-dioxo-5H-pyrano[2,3-c]isoquinoline-2-carboxylate
• CAS: 141990-70-7
• 化学式: C₁₇H₁₅NO₇
• 分子量: 345.309
• InChiKey: QGNUYCLOBXSMDG-UHFFFAOYSA-N

物化性质

• 沸点：
  691.3±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  107.83
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 8,9-dimethoxy-3,6-dioxo-5,6-dihydro-3H-pyran<2,3-c>isoquinoline-2-carboxylate 在 potassium tert-butylate 作用下， 以 硝基苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.67h， 生成 ethyl 9,10-dimethoxy-7-oxo-4,5-dihydro-7H-pyrrolo<3,2,1-de>phenanthridine-2-carboxylate
  参考文献：
  名称：

  Synthesis of Antitumor Lycorines by Intramolecular Diels−Alder Reaction

  摘要：

  Pharmacologically interesting lycorines were obtained by a short, efficient method based on an intramolecular Diels-Alder reaction between an alpha-pyrone and an alkyne, followed by loss of CO2 in a retro Diels-Alder reaction. The cyclization precursors (pyrones 9) were obtained in good yields in two or three steps from the corresponding homophthalic acid or anhydride.

  DOI：

  10.1021/jo9518415
• 作为产物：
  描述：

  4,5-dimethylhomophthalimide 在 sodium methylate 、 乙酸酐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 8,9-dimethoxy-3,6-dioxo-5,6-dihydro-3H-pyran<2,3-c>isoquinoline-2-carboxylate
  参考文献：
  名称：

  A new approach to the synthesis of antitumoralkaloids with the lycorane skeleton

  摘要：

  A new approach to the synthesis of lycorane-type alkaloids is described. The key step is intramolecular cycloaddition between an alpha-pyrone and an alkyne.

  DOI：

  10.1016/s0040-4039(00)74224-9

文献信息

• A new approach to the synthesis of antitumoralkaloids with the lycorane skeleton
  作者：Dolores Pérez、Enrique Guitián、Luis Castedo

  DOI：10.1016/s0040-4039(00)74224-9

  日期：1992.4

  A new approach to the synthesis of lycorane-type alkaloids is described. The key step is intramolecular cycloaddition between an alpha-pyrone and an alkyne.
• Synthesis of Antitumor Lycorines by Intramolecular Diels−Alder Reaction
  作者：Dolores Pérez、Gema Burés、Enrique Guitián、Luis Castedo

  DOI：10.1021/jo9518415

  日期：1996.1.1

  Pharmacologically interesting lycorines were obtained by a short, efficient method based on an intramolecular Diels-Alder reaction between an alpha-pyrone and an alkyne, followed by loss of CO2 in a retro Diels-Alder reaction. The cyclization precursors (pyrones 9) were obtained in good yields in two or three steps from the corresponding homophthalic acid or anhydride.