5-(benzoylhex-5-enoylamino)furan-2-carboxylic acid methyl ester | 208335-34-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(benzoylhex-5-enoylamino)furan-2-carboxylic acid methyl ester
• 英文别名: Methyl 5-[benzoyl(hex-5-enoyl)amino]furan-2-carboxylate
• CAS: 208335-34-6
• 化学式: C₁₉H₁₉NO₅
• 分子量: 341.364
• InChiKey: CBNHDLVLZJZVLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(benzoylhex-5-enoylamino)furan-2-carboxylic acid methyl ester 在 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 42.0h， 生成 5-[Benzoyl-(2-[1,3]dioxolan-2-yl-ethyl)-amino]-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
• 作为产物：
  描述：

  5-氨基-2-糠酸甲酯 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 37.0h， 生成 5-(benzoylhex-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).