ethyl-N-(5-methoxycarbonyl-2-furyl)carbaminate | 110189-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl-N-(5-methoxycarbonyl-2-furyl)carbaminate
• 英文别名: Methyl 5-(ethoxycarbonylamino)furan-2-carboxylate
• CAS: 110189-97-4
• 化学式: C₉H₁₁NO₅
• 分子量: 213.19
• InChiKey: LITVTFSIBXDFDF-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  280.7±25.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-溴-1-丁烯 、 ethyl-N-(5-methoxycarbonyl-2-furyl)carbaminate 在 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以86%的产率得到Methyl 5-[but-3-enyl(ethoxycarbonyl)amino]furan-2-carboxylate
  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 、 焦碳酸二乙酯 反应 24.0h， 以56%的产率得到ethyl-N-(5-methoxycarbonyl-2-furyl)carbaminate
  参考文献：
  名称：

  Stibranyi, Ladislav; Peeva, Milena; Kozempelova, Zdena, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 12, p. 2817 - 2825

  摘要：

  DOI：

文献信息

• STIBRANYI L.; PEEVA M.; KOZEMPELOVA Z.; LESKO J.; KOVAC J., COLLECT. CZECHOSL. CHEM. COMMUN., 51,(1986) N 12, 2817-2825
  作者：STIBRANYI L.、 PEEVA M.、 KOZEMPELOVA Z.、 LESKO J.、 KOVAC J.

  DOI：——

  日期：——
• 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).
• Stibranyi, Ladislav; Peeva, Milena; Kozempelova, Zdena, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 12, p. 2817 - 2825
  作者：Stibranyi, Ladislav、Peeva, Milena、Kozempelova, Zdena、Lesko, Jan、Kovac, Jaroslav

  DOI：——

  日期：——