4-(苯基氨基)丁腈 | 73747-25-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-(苯基氨基)丁腈
• 英文名称: 4-(phenylamino)butanenitrile
• 英文别名: Butyronitrile, 4-anilino-；4-anilinobutanenitrile
• CAS: 73747-25-8
• 化学式: C₁₀H₁₂N₂
• mdl: MFCD01737442
• 分子量: 160.219
• InChiKey: QMBPIQSHYXCCMR-UHFFFAOYSA-N

物化性质

• 沸点：
  138-140 °C(Press: 1 Torr)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(苯基氨基)丁腈 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以71%的产率得到1-苯基-2-吡咯烷酮
  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
• 作为产物：
  描述：

  1-phenyl-1,4,5,6-tetrahydropyridazin-3(2H)-one 在 四(三苯基膦)钯 sodium carbonate 、 三氯氧磷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.08h， 生成 4-(苯基氨基)丁腈
  参考文献：
  名称：

  Microwave-assisted cross-coupling of 3-chloro-2-pyrazolines and 3-chloro-1-phenyl-1,4,5,6-tetrahydropyridazine with aryl boronic acids

  摘要：

  3-Chloro-l-phenyl-2-pyrazoliiie and 3-chloo-1-phenyl-1,4,5,6-tetrahydropyridazine were coupled with aryl boronic acids in good yields under microwave heating conditions (140 degrees C, 5 min). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.075

文献信息

• Visible-Light Photoredox-Catalyzed Giese Reaction: Decarboxylative Addition of Amino Acid Derived α-Amino Radicals to Electron-Deficient Olefins
  作者：Anthony Millet、Quentin Lefebvre、Magnus Rueping

  DOI：10.1002/chem.201602257

  日期：2016.9.12

  A tin‐ and halide‐free, visible‐light photoredox‐catalyzed Giese reaction was developed. Primary and secondary α‐amino radicals were generated readily from amino acids in the presence of catalytic amounts of an iridium photocatalyst. The reactivity of the α‐amino radicals has been evaluated for the functionalization of a variety of activated olefins.

  开发了一种无锡和无卤可见光氧化还原催化的Giese反应。在催化量的铱光催化剂存在下，氨基酸很容易产生伯和仲α-氨基。已经评估了α-氨基自由基的反应性，以用于各种活化烯烃的功能化。
• Microwave-assisted cyclizations promoted by polyphosphoric acid esters: a general method for 1-aryl-2-iminoazacycloalkanes
  作者：Jimena E Díaz、María C Mollo、Liliana R Orelli

  DOI：10.3762/bjoc.12.190

  日期：——

  omega-arylaminonitriles promoted by polyphosphoric acid (PPA) esters. 1-Aryl-2-iminopyrrolidines were easily prepared from the acyclic precursors employing a chloroformic solution of ethyl polyphosphate (PPE). The use of trimethylsilyl polyphosphate (PPSE) in solvent-free conditions allowed for the synthesis of 1-aryl-2-iminopiperidines and hitherto unreported 1-aryl-2-iminoazepanes. The cyclization reaction involves

  通过微波辅助由多磷酸（PPA）酯促进的ω-芳基氨基腈的闭环反应，提出了合成5至7元1-芳基-2-亚氨基氮杂氮杂环烷的第一个通用程序。1-芳基-2-亚氨基吡咯烷易于使用聚磷酸乙酯（PPE）的氯甲酸溶液由无环前体制备。在无溶剂条件下使用多甲基三甲基甲硅烷基多磷酸酯（PPSE）可以合成1-芳基-2-亚氨基哌啶和迄今未报道的1-芳基-2-亚氨基氮庚酮。环化反应涉及高到高产率和短反应时间，并且代表了PPA酯在杂环合成中的新应用。
• Minimization of Back‐Electron Transfer Enables the Elusive sp ³ C−H Functionalization of Secondary Anilines
  作者：Huaibo Zhao、Daniele Leonori

  DOI：10.1002/anie.202100051

  日期：2021.3.29

  Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N‐Dialkyl‐derivatives enable radical generation α to the N‐atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back‐electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence

  苯胺是光诱导电子转移中最常用的一类底物。 N,N-二烷基衍生物能够通过氧化然后去质子化使 N 原子产生自由基 α。然而，由于快速反电子转移（BET），这种方法对于单取代苯胺来说难以捉摸。在这里，我们证明了在外源烷基胺存在的情况下使用光氧化还原催化可以最大限度地减少 BET。这种方法协同帮助苯胺 SET 氧化，然后加速随后的去质子化。通过这种方式，现在可以生成 α-苯胺烷基自由基，并且这些物质可以在一般意义上用于实现不同的 sp 3 C−H 官能化。
• 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。
• Reductive and Catalytic Monoalkylation of Primary Amines Using Nitriles as an Alkylating Reagent
  作者：Hironao Sajiki、Takashi Ikawa、Kosaku Hirota

  DOI：10.1021/ol047871o

  日期：2004.12.1

  and catalytic mono-N-alkylation method of both aromatic and aliphatic amines using nitriles as an alkylating agent with Pd/C or Rh/C as a catalyst is described. This method is particularly attractive to provide an environmentally benign and applicable alkylation method of amines without using toxic and corrosive alkylating agents such as alkyl halides and carbonyl compounds.

  [反应：参见正文]描述了使用腈作为烷基化剂，以Pd / C或Rh / C为催化剂的芳香族和脂肪族胺的选择性催化单N-烷基化方法。该方法对于提供一种环境友好的胺的烷基化方法而不使用有毒和腐蚀性的烷基化剂（例如卤代烷和羰基化合物）特别有吸引力。