ethyl 8,9-(methylenedioxy)-3,6-dioxo-5,6-dihydro-3H-pyran<2,3-c>isoquinoline-2-carboxylate | 174866-32-1

• 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: ethyl 8,9-(methylenedioxy)-3,6-dioxo-5,6-dihydro-3H-pyran<2,3-c>isoquinoline-2-carboxylate
• 英文别名: Ethyl 5,9-dioxo-6,13,15-trioxa-8-azatetracyclo[8.7.0.02,7.012,16]heptadeca-1(17),2(7),3,10,12(16)-pentaene-4-carboxylate
• CAS: 174866-32-1
• 化学式: C₁₆H₁₁NO₇
• 分子量: 329.266
• InChiKey: PSORXDXLNSBRRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  对甲苯磺酸 3-丁炔酯 、 ethyl 8,9-(methylenedioxy)-3,6-dioxo-5,6-dihydro-3H-pyran<2,3-c>isoquinoline-2-carboxylate 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以35%的产率得到ethyl 6-(3-butynyloxy)-8,9-(methylenedioxy)-3-oxo-3H-pyran<2,3-c>isoquinoline-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：

  6,7-(methylenedioxy)homophthalimide 在 盐酸 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 ethyl 8,9-(methylenedioxy)-3,6-dioxo-5,6-dihydro-3H-pyran<2,3-c>isoquinoline-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