2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione | 174866-34-3

• 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: 2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione
• 英文别名: 6-but-3-ynyl-8H-[1,3]dioxolo[4,5-g]isoquinoline-5,7-dione
• CAS: 174866-34-3
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: ZMKCWHVBDMBKTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione 在 氢氧化钾 、 copper bronze 作用下， 以 硝基苯 为溶剂， 反应 9.92h， 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：

  4,5-methylenedioxyhomophthalic anhydride 、 1-氨基-3-丁炔 以 二氯甲烷 为溶剂， 反应 20.0h， 以79%的产率得到2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione
  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.