5-(hex-5-enoylamino)furan-2-carboxylic acid methyl ester | 208335-91-5

• 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-(hex-5-enoylamino)furan-2-carboxylic acid methyl ester
• 英文别名: Methyl 5-(hex-5-enoylamino)furan-2-carboxylate
• CAS: 208335-91-5
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: HQIUHJCQBJCKRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-(hex-5-enoylamino)furan-2-carboxylic acid methyl ester 在 三乙胺 作用下， 以 甲苯 、 苯 为溶剂， 反应 60.0h， 生成 N-5-carbomethoxyfuran-2-ylbenzamide
  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：

  5-氨基-2-糠酸甲酯 、 5-己酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到5-(hex-5-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

文献信息

• IMDAF Cycloaddition as a Method for the Preparation of Pyrrolophenanthridine Alkaloids
  作者：Albert Padwa、Martin Dimitroff、Alex G. Waterson、Tianhua Wu

  DOI：10.1021/jo980008f

  日期：1998.6.1

  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).