4-(indolin-1-yl)butanenitrile | 7633-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(indolin-1-yl)butanenitrile
• 英文别名: 1-Indolin-butyronitril；4-(2,3-Dihydroindol-1-yl)butanenitrile
• CAS: 7633-34-3
• 化学式: C₁₂H₁₄N₂
• mdl: MFCD09933255
• 分子量: 186.257
• InChiKey: CUIDPPXVCGEDCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚啉 、 cyclobutanone O-(4-(trifluoromethyl)benzoyl) oxime 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以80%的产率得到4-(indolin-1-yl)butanenitrile
  参考文献：
  名称：

  Single-Electron-Transfer-Induced C(sp³)–N Couplings via C–C Bond Cleavage of Cycloketoxime Esters

  摘要：

  A practical single-electron-transfer-induced selective C(sp(3))-N coupling of cycloketoximes with anilines via C-C bond cleavage under copper-catalytic and synergetic photoredox/copper-catalytic reaction systems has been uncovered. These two powerful and simple protocols demonstrated excellent selectivity and good functional group compatibility without any base or ligand control. Preliminary mechanistic experiments indicated that a radical-mediated process was involved in these transformations.

  DOI：

  10.1021/acs.joc.9b01338

文献信息

• Copper-catalyzed ring-opening C(sp³)–N coupling of cycloketone oxime esters: access to 1°, 2° and 3° alkyl amines
  作者：Li Tian、Shuangqiu Gao、Rui Wang、Yang Li、Chunlin Tang、Lili Shi、Junkai Fu

  DOI：10.1039/c9cc02030f

  日期：——

  A novel copper-catalyzed C(sp3)–N coupling of cycloketone oxime esters with nitrogen nucleophiles has been realized. All of the N-aryl/alkylanilines, anilines and benzophenone imine could be employed in this protocol to produce a variety of 1°, 2° and 3° alkyl amines in one or two steps. These resultant cyano-containing alkyl amines were proven to be versatile synthetic building blocks in a variety

  已经实现了一种新型的铜催化的环酮肟酯与氮亲核试剂的C（sp 3）-N偶联。所有N-芳基/烷基苯胺，苯胺和二苯甲酮亚胺都可以在此方案中使用，以一步或两步生产各种1°，2°和3°烷基胺。这些生成的含氰基烷基胺被证明是在各种化学转化中的通用合成构件。