4-(5-nitrofuran-2-yl)morpholine | 4818-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 4-(5-nitrofuran-2-yl)morpholine
• 英文别名: 5-(4-morpholinyl)-2-nitrofuran；4-(5-nitro-furan-2-yl)-morpholine；2-Nitro-5-morpholino-furan；Morpholine, 4-(5-nitro-2-furanyl)-
• CAS: 4818-48-8
• 化学式: C₈H₁₀N₂O₄
• 分子量: 198.178
• InChiKey: CKWVBMYVQJWULV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(5-nitrofuran-2-yl)morpholine 在 溶剂黄146 、 锌 作用下， 反应 0.5h， 以30%的产率得到4-morpholino-4-oxobutanenitrile
  参考文献：
  名称：

  A Remarkable Reductive Dearomatization of Thiophene and Furan Rings

  摘要：

  Reduction of a 2-nitrothiophene 4 and the corresponding 2-nitrofuran 20 with zinc and acetic acid produced a remarkable dearomatization and fragmentation reaction to give acyclic nitriles 6 and 22, respectively. The intermediate 2-aminothiophene 5 was trapped by acylation with acetic anhydride to give acetamide 7. An additional acrylonitrile intermediate 17 was also trapped by Michael addition with benzyl mercaptan to give adduct 18. An alternate synthesis of nitrile 22 produced in the reduction of nitrofuran 20 provided an authentic sample of the product. The conversion of nitroaromatic heterocycles 4 and 20 into aliphatic nitriles 6 and 22 are remarkable and unprecedented reactions.

  DOI：

  10.1055/s-0033-1338416
• 作为产物：
  描述：

  吗啉 、 2,5-二硝呋喃 以 乙醚 为溶剂， 反应 2.5h， 以97%的产率得到4-(5-nitrofuran-2-yl)morpholine
  参考文献：
  名称：

  Diels−Alder Reaction of 2-Amino-Substituted Furans as a Method for Preparing Substituted Anilines

  摘要：

  5-Amino-2-furancarboxylic acid methyl ester undergoes a facile Diels-Alder cycloaddition with a variety of dienophiles to afford ring-opened cycloadducts that are readily dehydrated using BF3 . OEt2 to give polysubstituted anilines. In each case, the cycloaddition proceeds with high regioselectivity, with the electron-withdrawing group being located ortho to the amino group. The most favorable FMO interaction is between the HOMO of the furanamine and the LUMO of the dienophile. The atomic coefficient at the ester carbon of the furan is larger than that at the amino center, and this nicely accommodates the observed regioselectivity. The [4 + 2]-cycloaddition of N-(5-nitrofuranyl)morpholine with methyl vinyl ketone affords a mixture of three phenols. One of the phenols is derived from a Diels-Alder reaction followed by nitro group ejection and subsequent aromatization. The remaining two phenols are the result of cleavage of the initially formed oxabicyclic intermediate with concomitant migration of the nitro group. The mild reaction conditions with which furan-2-carbamic acid tert-butyl ester undergoes Diels-Alder cycloaddition with N-phenylmaleimide allow for the ready isolation of the initial oxybridged cycloadduct.

  DOI：

  10.1021/jo9702599

文献信息

• Diels−Alder Reaction of 2-Amino-Substituted Furans as a Method for Preparing Substituted Anilines
  作者：Albert Padwa、Martin Dimitroff、Alex G. Waterson、Tianhua Wu

  DOI：10.1021/jo9702599

  日期：1997.6.13

  5-Amino-2-furancarboxylic acid methyl ester undergoes a facile Diels-Alder cycloaddition with a variety of dienophiles to afford ring-opened cycloadducts that are readily dehydrated using BF3 . OEt2 to give polysubstituted anilines. In each case, the cycloaddition proceeds with high regioselectivity, with the electron-withdrawing group being located ortho to the amino group. The most favorable FMO interaction is between the HOMO of the furanamine and the LUMO of the dienophile. The atomic coefficient at the ester carbon of the furan is larger than that at the amino center, and this nicely accommodates the observed regioselectivity. The [4 + 2]-cycloaddition of N-(5-nitrofuranyl)morpholine with methyl vinyl ketone affords a mixture of three phenols. One of the phenols is derived from a Diels-Alder reaction followed by nitro group ejection and subsequent aromatization. The remaining two phenols are the result of cleavage of the initially formed oxabicyclic intermediate with concomitant migration of the nitro group. The mild reaction conditions with which furan-2-carbamic acid tert-butyl ester undergoes Diels-Alder cycloaddition with N-phenylmaleimide allow for the ready isolation of the initial oxybridged cycloadduct.
• A Remarkable Reductive Dearomatization of Thiophene and Furan Rings
  作者：Norton Peet、Son Nguyen、Xiaoyuan Ding

  DOI：10.1055/s-0033-1338416

  日期：——

  Reduction of a 2-nitrothiophene 4 and the corresponding 2-nitrofuran 20 with zinc and acetic acid produced a remarkable dearomatization and fragmentation reaction to give acyclic nitriles 6 and 22, respectively. The intermediate 2-aminothiophene 5 was trapped by acylation with acetic anhydride to give acetamide 7. An additional acrylonitrile intermediate 17 was also trapped by Michael addition with benzyl mercaptan to give adduct 18. An alternate synthesis of nitrile 22 produced in the reduction of nitrofuran 20 provided an authentic sample of the product. The conversion of nitroaromatic heterocycles 4 and 20 into aliphatic nitriles 6 and 22 are remarkable and unprecedented reactions.