2-(1H-pyrrol-2-ylmethylene)succinic acid 1-methyl ester | 41174-61-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(1H-pyrrol-2-ylmethylene)succinic acid 1-methyl ester
• 英文别名: (E)-3-methoxycarbonyl-4-(1H-pyrrol-2-yl)but-3-enoic acid
• CAS: 41174-61-2
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: DHIOOPMOJWVPIO-FNORWQNLSA-N

物化性质

• 熔点：
  134-136 °C
• 沸点：
  432.7±40.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-(1H-pyrrol-2-ylmethylene)succinic acid 1-methyl ester 在 三乙胺 作用下， 反应 1.0h， 生成 Methyl 5-acetyloxyindolizine-7-carboxylate
  参考文献：
  名称：

  A Reinvestigation of 4-Hydroxyindole-6-carboxylate Synthesis from Pyrrole-2-carboxaldehyde:  A Facile Synthesis of Indoles and Indolizines

  摘要：

  Cyclization of the Stobbe product 3 under the literature conditions (acetic anhydride/sodium acetate) affords both the indole 6 and the indolizine 8. The presence of base promotes the formation of indolizine products, and using acetic anhydride/triethylamine leads to indolizine products in good yield. Improved conditions for conversion to indoles 2, 5, and 6 are reported, and inconsistencies in some of the literature structure assignments and characterization data are noted.

  DOI：

  10.1021/jo040191e
• 作为产物：
  描述：

  2-吡咯甲醛 、 丁二酸二甲酯 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 16.0h， 生成 2-(1H-pyrrol-2-ylmethylene)succinic acid 1-methyl ester
  参考文献：
  名称：

  A Reinvestigation of 4-Hydroxyindole-6-carboxylate Synthesis from Pyrrole-2-carboxaldehyde:  A Facile Synthesis of Indoles and Indolizines

  摘要：

  Cyclization of the Stobbe product 3 under the literature conditions (acetic anhydride/sodium acetate) affords both the indole 6 and the indolizine 8. The presence of base promotes the formation of indolizine products, and using acetic anhydride/triethylamine leads to indolizine products in good yield. Improved conditions for conversion to indoles 2, 5, and 6 are reported, and inconsistencies in some of the literature structure assignments and characterization data are noted.

  DOI：

  10.1021/jo040191e