N-[3-cyano-5-(4-methylphenyl)-2-furanyl]acetamide | 453590-33-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[3-cyano-5-(4-methylphenyl)-2-furanyl]acetamide
• 英文别名: N-[3-cyano-5-(4-methylphenyl)furan-2-yl]acetamide
• CAS: 453590-33-5
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: HNLQHUCPSVSQOS-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[3-cyano-5-(4-methylphenyl)-2-furanyl]acetamide 、 5-溴-1-戊烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.0h， 以56%的产率得到N-[3-cyano-5-(4-methylphenyl)-2-furanyl]-N-4-penten-1-ylacetamide
  参考文献：
  名称：

  Synthesis of Dihydroindoles and Tetrahydroquinolines by the Intramolecular Diels-Alder Reaction of N-Alkenylated 2-Acylamino-3-furancarbonitriles

  摘要：

  An approach to dihydroindoles and tetrahydroquinolines from N-alkenylated 2-acylamino-3-furancarbonitriles via a [4 + 2] cycloaddition reaction is described. Thermal treatment of N-alkenylated 2-acylamino-3-furancarbonitriles 5a-d, 6a-d, 9a-d, and 10a-d, which were prepared from 2-acylamino-3-furancarbonitriles 3a-d and/or 4a-d and 4-bromo-1-butene and/or 5-bromo-1-pentene, caused an intramolecular Diels-Alder reaction to give the corresponding dihydroindole and tetrahydroquinoline derivatives 7a-d, 8a-d, 11a-d, and 12a-d. This method has the advantage of easier work-up procedure.

  DOI：

  10.3987/com-10-11936
• 作为产物：
  描述：

  C₁₆H₁₄N₂O₃ 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以3.62 g的产率得到N-[3-cyano-5-(4-methylphenyl)-2-furanyl]acetamide
  参考文献：
  名称：

  Synthesis of Dihydroindoles and Tetrahydroquinolines by the Intramolecular Diels-Alder Reaction of N-Alkenylated 2-Acylamino-3-furancarbonitriles

  摘要：

  An approach to dihydroindoles and tetrahydroquinolines from N-alkenylated 2-acylamino-3-furancarbonitriles via a [4 + 2] cycloaddition reaction is described. Thermal treatment of N-alkenylated 2-acylamino-3-furancarbonitriles 5a-d, 6a-d, 9a-d, and 10a-d, which were prepared from 2-acylamino-3-furancarbonitriles 3a-d and/or 4a-d and 4-bromo-1-butene and/or 5-bromo-1-pentene, caused an intramolecular Diels-Alder reaction to give the corresponding dihydroindole and tetrahydroquinoline derivatives 7a-d, 8a-d, 11a-d, and 12a-d. This method has the advantage of easier work-up procedure.

  DOI：

  10.3987/com-10-11936

文献信息

• Synthesis of Dihydroindoles and Tetrahydroquinolines by the Intramolecular Diels-Alder Reaction of N-Alkenylated 2-Acylamino-3-furancarbonitriles
  作者：Hiroshi Maruoka、Fumi Okabe、Yoshimichi Koutake、Eiichi Masumoto、Toshihiro Fujioka、Kenji Yamagata

  DOI：10.3987/com-10-11936

  日期：——

  An approach to dihydroindoles and tetrahydroquinolines from N-alkenylated 2-acylamino-3-furancarbonitriles via a [4 + 2] cycloaddition reaction is described. Thermal treatment of N-alkenylated 2-acylamino-3-furancarbonitriles 5a-d, 6a-d, 9a-d, and 10a-d, which were prepared from 2-acylamino-3-furancarbonitriles 3a-d and/or 4a-d and 4-bromo-1-butene and/or 5-bromo-1-pentene, caused an intramolecular Diels-Alder reaction to give the corresponding dihydroindole and tetrahydroquinoline derivatives 7a-d, 8a-d, 11a-d, and 12a-d. This method has the advantage of easier work-up procedure.