4-morpholino-4-oxobutanenitrile | 1267908-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-morpholino-4-oxobutanenitrile
• 英文别名: 4-Morpholin-4-yl-4-oxobutanenitrile；4-morpholin-4-yl-4-oxobutanenitrile
• CAS: 1267908-02-0
• 化学式: C₈H₁₂N₂O₂
• 分子量: 168.195
• InChiKey: BFHIWWWJBFSBLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  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

文献信息

• A Visible Light Driven Nickel Carbonylation Catalyst: The Synthesis of Acid Chlorides from Alkyl Halides
  作者：Kristian El Chami、Yi Liu、Mohammed A. Belahouane、Yiyang Ma、Pierre‐Louis Lagueux‐Tremblay、Bruce A. Arndtsen

  DOI：10.1002/anie.202213297

  日期：2023.3

  A visible light driven nickel carbonylation catalyst has been develop. This offers a method for carbonylative coupling reactions with an earth abundant metal at ambient temperature for the conversion of alkyl halides into synthetically versatile acid chlorides. The acid chlorides can then be transformed into an array of challenging ester, thioester and amide products.

  已经开发出可见光驱动的镍羰基化催化剂。这提供了一种在环境温度下与地球上丰富的金属进行羰基化偶联反应的方法，用于将卤代烷转化为合成用途广泛的酰氯。然后可以将酰氯转化为一系列具有挑战性的酯、硫酯和酰胺产品。
• 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.