2-(N-cyclohexylamino)-3-phenyl-4-acetyl-5-methylfuran

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(N-cyclohexylamino)-3-phenyl-4-acetyl-5-methylfuran
• 英文别名: 4-acetyl-2-(N-cyclohexylamino)-5-methyl-3-phenylfuran；1-[5-(cyclohexylamino)-2-methyl-4-phenylfuran-3-yl]ethanone
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: BTNLYZNVQIGSCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异氰环已烷 、 3-亚苄基-2,4-戊二酮 以 二氯甲烷 为溶剂， 反应 5.0h， 以76%的产率得到2-(N-cyclohexylamino)-3-phenyl-4-acetyl-5-methylfuran
  参考文献：
  名称：

  On the reaction between alkyl isocyanides and 3-benzylidene-2,4-pentanedione. A convenient synthetic route to densely functionalized furans

  摘要：

  Alkyl isocyanides undergo a formal [1 + 4] cycloaddition reaction with 3-benzylidene-2,4-pentanedione yielding multiply functionalized furan ring systems in fairly high yields. The H-1 NMR spectrum of 4-acetyl-2-(N-benzylamino)-5-methyl-3-phenylfuran shows an AB pattern for the benzylic methylene protons as a result of a restricted rotation about the bond between the acetyl group and the furan ring, thus giving rise to perpendicular disymmetric planes.

  DOI：

  10.1007/bf00807601

文献信息

• Tandem oxidative isocyanide-based cycloaddition reactions in the presence of MIL-101(Cr) as a reusable solid catalyst
  作者：Ahmad Shaabani、Heshmatollah Sepahvand、Mostafa M. Amini、Alireza Hashemzadeh、Mahmoud Borjian Boroujeni、Elham Badali

  DOI：10.1016/j.tet.2018.02.046

  日期：2018.4

  The tandem oxidative three-component synthesis of two types of the heterocycles such as furans and imidazopyridines, via isocyanides [1+4] cycloaddition reactions in the presence of MIL-101(Cr) under aerobic conditions are reported. When the 4-toluenesulfonylmethyl isocyanide was used, an unexpected [3+2] cycloaddition reaction of isocyanides with aldehydes accomplished and dihydrophenyloxazoles and

  报道了在有氧条件下，在MIL-101（Cr）存在下，通过异氰酸酯[1 + 4]环加成反应，串联合成了两种类型的杂环（例如呋喃和咪唑并吡啶）的氧化三组分串联反应。当使用4-甲苯磺酰基甲基异氰酸酯时，异氰酸酯与醛的意外的[3 + 2]环加成反应完成，并生成了二氢苯基恶唑和苯基恶唑。这些合成成功地使用了广泛的底物进行。
• On the reaction between alkyl isocyanides and 3-benzylidene-2,4-pentanedione. A convenient synthetic route to densely functionalized furans
  作者：I. Yavari、A. Shaabani、M. T. Maghsoodlou

  DOI：10.1007/bf00807601

  日期：——

  Alkyl isocyanides undergo a formal [1 + 4] cycloaddition reaction with 3-benzylidene-2,4-pentanedione yielding multiply functionalized furan ring systems in fairly high yields. The H-1 NMR spectrum of 4-acetyl-2-(N-benzylamino)-5-methyl-3-phenylfuran shows an AB pattern for the benzylic methylene protons as a result of a restricted rotation about the bond between the acetyl group and the furan ring, thus giving rise to perpendicular disymmetric planes.