5-(pent-4-enoylamino)furan-2-carboxylic acid methyl ester | 208334-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-(pent-4-enoylamino)furan-2-carboxylic acid methyl ester
• 英文别名: Methyl 5-(pent-4-enoylamino)furan-2-carboxylate
• CAS: 208334-93-4
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: NEURZZVDKAIMHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(pent-4-enoylamino)furan-2-carboxylic acid methyl ester 以 甲苯 为溶剂， 反应 24.0h， 以66%的产率得到2-氧代-1,2,3,4-四氢喹啉-6-羧酸甲酯
  参考文献：
  名称：

  IMDAF Cycloaddition as a Method for the Preparation of Pyrrolophenanthridine Alkaloids

  摘要：

  Acylation of 5-amino-2-furancarboxylic acid methyl ester with alkenoyl acid chlorides gives 2-amidofurans that undergo intramolecular Diels-Alder cycloadditions. The reactions occur at 165 degrees C in toluene or at 100 degrees C when 4 M ethereal LiClO4 was used as the solvent. The resultant dihydroindoles are formed by the nitrogen lone pair assisted ring opening of the initial era-bridged cycloadducts, followed by loss of water. Under certain conditions, alternative cationic cyclization routes become important pathways. Several members of the pyrrolophenanthridine class of alkaloids were obtained by a short, efficient method based on the intramolecular Diels-Alder furan cycloaddition of 2-amidofurans containing a tethered alkenyl group. The resulting dihydroindoles were elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system by a free radical induced cyclization using bis(tributyltin).

  DOI：

  10.1021/jo980008f
• 作为产物：
  描述：

  4-戊烯酸 在 吡啶 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 5-(pent-4-enoylamino)furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  IMDAF Cycloaddition as a Method for the Preparation of Pyrrolophenanthridine Alkaloids

  摘要：

  Acylation of 5-amino-2-furancarboxylic acid methyl ester with alkenoyl acid chlorides gives 2-amidofurans that undergo intramolecular Diels-Alder cycloadditions. The reactions occur at 165 degrees C in toluene or at 100 degrees C when 4 M ethereal LiClO4 was used as the solvent. The resultant dihydroindoles are formed by the nitrogen lone pair assisted ring opening of the initial era-bridged cycloadducts, followed by loss of water. Under certain conditions, alternative cationic cyclization routes become important pathways. Several members of the pyrrolophenanthridine class of alkaloids were obtained by a short, efficient method based on the intramolecular Diels-Alder furan cycloaddition of 2-amidofurans containing a tethered alkenyl group. The resulting dihydroindoles were elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system by a free radical induced cyclization using bis(tributyltin).

  DOI：

  10.1021/jo980008f