5-methoxycarbonyloxyindolizine-7-carboxylic acid methyl ester | 784150-88-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 5-methoxycarbonyloxyindolizine-7-carboxylic acid methyl ester
• 英文别名: Methyl 5-((methoxycarbonyl)oxy)indolizine-7-carboxylate；methyl 5-methoxycarbonyloxyindolizine-7-carboxylate
• CAS: 784150-88-5
• 化学式: C₁₂H₁₁NO₅
• 分子量: 249.223
• InChiKey: MGMSRGYBSORIHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸甲酯 、 5-methoxycarbonyloxyindolizine-7-carboxylic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以84%的产率得到5-methoxyindolizine-7-carboxylic acid 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
• 作为产物：
  描述：

  氯甲酸甲酯 、 2-(1H-pyrrol-2-ylmethylene)succinic acid 1-methyl ester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到5-methoxycarbonyloxyindolizine-7-carboxylic acid 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

文献信息

• A Reinvestigation of 4-Hydroxyindole-6-carboxylate Synthesis from Pyrrole-2-carboxaldehyde:  A Facile Synthesis of Indoles and Indolizines
  作者：Musong Kim、Edwin Vedejs

  DOI：10.1021/jo040191e

  日期：2004.10.1

  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.