ethyl 9,10-(methylenedioxy)-7-oxo-4,5-dihydro-7H-pyrrolo<3,2,1-de>phenanthridine-2-carboxylate | 174866-37-6

• 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: ethyl 9,10-(methylenedioxy)-7-oxo-4,5-dihydro-7H-pyrrolo<3,2,1-de>phenanthridine-2-carboxylate
• 英文别名: Ethyl 11-oxo-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9,15(19),16-hexaene-17-carboxylate
• CAS: 174866-37-6
• 化学式: C₁₉H₁₅NO₅
• 分子量: 337.332
• InChiKey: IKBPOTJEGSZYQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 9,10-(methylenedioxy)-7-oxo-4,5-dihydro-7H-pyrrolo<3,2,1-de>phenanthridine-2-carboxylate 在 氢氧化钾 、 copper bronze 作用下， 生成 去氢石蒜碱酮
  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：

  2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione 以 硝基苯 为溶剂， 反应 7.17h， 生成 ethyl 9,10-(methylenedioxy)-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

文献信息

• 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.