3-ethoxycarbonylindolizine-1,2-dicarboxylic anhydride | 309975-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 3-ethoxycarbonylindolizine-1,2-dicarboxylic anhydride
• 英文别名: Ethyl 1,3-dioxofuro[3,4-a]indolizine-4-carboxylate
• CAS: 309975-37-9
• 化学式: C₁₃H₉NO₅
• 分子量: 259.218
• InChiKey: KNXBKEBZOOQJOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonylindolizine-1,2-dicarboxylic anhydride 在 copper chromite 作用下， 以 四氢呋喃 、 喹啉 为溶剂， 反应 1.5h， 生成 ethyl 2-benzoylindolizine-3-carboxylate
  参考文献：
  名称：

  Reaction of 3-Ethoxycarbonyl- indolizine-1,2-dicarboxylic Anhydride: Synthesis of 2-Acylindolizines and Quinones

  摘要：

  Reaction of indolizine-1,2-dicarboxylic anhydride with Grignard reagents gave 2-acylindolizine-1-carboxylic acids, which were converted to 2-acylindolizines. The anhydride reacted with anisole in the presence of titanium chloride(IV) to afford 2-(4-methoxybenzoyl)indolizine-1-carboxylic acid, which was also led to 2-(4-methoxybenzoyl)indolizine. Successive treatment of the 2-acylindolizine-1-carboxylic acids with phosphorus pentachloride and aluminum(III) chloride provided the corresponding quinones.

  DOI：

  10.3987/com-00-8950
• 作为产物：
  描述：

  1-(2-乙氧基-2-氧乙基)溴化吡啶 在 potassium carbonate 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 98.0h， 生成 3-ethoxycarbonylindolizine-1,2-dicarboxylic anhydride
  参考文献：
  名称：

  Reaction of 3-Ethoxycarbonyl- indolizine-1,2-dicarboxylic Anhydride: Synthesis of 2-Acylindolizines and Quinones

  摘要：

  Reaction of indolizine-1,2-dicarboxylic anhydride with Grignard reagents gave 2-acylindolizine-1-carboxylic acids, which were converted to 2-acylindolizines. The anhydride reacted with anisole in the presence of titanium chloride(IV) to afford 2-(4-methoxybenzoyl)indolizine-1-carboxylic acid, which was also led to 2-(4-methoxybenzoyl)indolizine. Successive treatment of the 2-acylindolizine-1-carboxylic acids with phosphorus pentachloride and aluminum(III) chloride provided the corresponding quinones.

  DOI：

  10.3987/com-00-8950

文献信息

• Reaction of 3-Ethoxycarbonylindoli-zine-1,2-dicarboxylic Anhydride with (3-Bromo-4-pyridyl)triisopropoxy- titanium: Synthesis of 5,12-Dimethyl- indolizino[2,1-g]isoquinoline (Ellip - ticine Analogue)
  作者：Yasuyoshi Miki、Noriko Nakamura、Ryota Yamakawa、Hajime Hibino、Hiroko Hachiken、Ko-ichi Matsushita

  DOI：10.3987/com-00-8993

  日期：——

  Reaction of indolizine-1,2-dicarboxylic anhydride with (3-bromo-4-pyridyl)triisopropoxytitanium gave 2-(3-bromoisonicotinoyl)-3-ethoxycarbonyl-indolizine-1-carboxylic acid as the sole product. The indolizine-l-carboxylic acid could be converted to 5,12-dimethylindolizine[2,1-g] isoquinoline in six steps.
• Reaction of 3-Ethoxycarbonyl- indolizine-1,2-dicarboxylic Anhydride: Synthesis of 2-Acylindolizines and Quinones
  作者：Yasuyoshi Miki、Noriko Nakamura、Ryota Yamakawa、Hiroko Hachiken、Ko-ichi Matsushita

  DOI：10.3987/com-00-8950

  日期：——

  Reaction of indolizine-1,2-dicarboxylic anhydride with Grignard reagents gave 2-acylindolizine-1-carboxylic acids, which were converted to 2-acylindolizines. The anhydride reacted with anisole in the presence of titanium chloride(IV) to afford 2-(4-methoxybenzoyl)indolizine-1-carboxylic acid, which was also led to 2-(4-methoxybenzoyl)indolizine. Successive treatment of the 2-acylindolizine-1-carboxylic acids with phosphorus pentachloride and aluminum(III) chloride provided the corresponding quinones.