α-methyl-α-(phenylamino)benzenepropanenitrile | 203123-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-methyl-α-(phenylamino)benzenepropanenitrile
• 英文别名: 2-Methyl-3-phenyl-2-(phenylamino)propionitrile；2-Anilino-2-methyl-3-phenylpropanenitrile
• CAS: 203123-40-4
• 化学式: C₁₆H₁₆N₂
• 分子量: 236.316
• InChiKey: KEWRIYODCHNMBC-UHFFFAOYSA-N

物化性质

• 溶解度：
  18.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  α-methyl-α-(phenylamino)benzenepropanenitrile 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 3-苯基-4-羟基喹啉-2(1H)-酮
  参考文献：
  名称：

  Synthesis of 4-hydroxy-2(1H)-pyridones from azomethines and substituted dialkylmalonates

  摘要：

  The reaction of azomethines 4 with substituted dialkyl malonates 5 leads to the formation of 3-substituted 4-hydroxy-2(1H)-pyridones 6 in moderate yields. The azomethines 4 are prepared via arylaminopropionitriles 3 or in the conventional way by acid catalyzed condensation of ketones 1 with anilines 2. Chlorination of pyridones 6 with sulfuryl chloride leads to compounds 8-10.

  DOI：

  10.1007/bf00806968
• 作为产物：
  描述：

  氰化钠 、 苯胺 、 苯基丙酮 以 溶剂黄146 为溶剂， 以85%的产率得到α-methyl-α-(phenylamino)benzenepropanenitrile
  参考文献：
  名称：

  Synthesis of 4-hydroxy-2(1H)-pyridones from azomethines and substituted dialkylmalonates

  摘要：

  The reaction of azomethines 4 with substituted dialkyl malonates 5 leads to the formation of 3-substituted 4-hydroxy-2(1H)-pyridones 6 in moderate yields. The azomethines 4 are prepared via arylaminopropionitriles 3 or in the conventional way by acid catalyzed condensation of ketones 1 with anilines 2. Chlorination of pyridones 6 with sulfuryl chloride leads to compounds 8-10.

  DOI：

  10.1007/bf00806968

文献信息

• Nafion–Fe: A New Efficient “Green” Lewis Acid Catalyst for the Ketonic Strecker Reaction
  作者：G. K. Surya Prakash、Inessa Bychinskaya、Eric R. Marinez、Thomas Mathew、George A. Olah

  DOI：10.1007/s10562-012-0958-2

  日期：2013.4

  yields and high purity by the Strecker reaction from ketones, aliphatic/aromatic amines and TMSCN using a new “green” Lewis acid catalyst, Nafion–Fe (iron Nafionate, Fe(III) salt of Nafion–H, a solid polymeric perfluoroalkanesulfonic acid) under conventional thermal as well as microwave conditions. Microwave and solvent-free conditions applied in this method shorten the reaction times, improve the yields

  使用新的“绿色”路易斯酸催化剂 Nafion，通过从酮、脂肪族/芳香族胺和 TMSCN 的 Strecker 反应，以中等至高产率和高纯度合成各种 α-氨基腈，α-氨基酸的前体–Fe（Nafionate 铁，Nafion-H 的 Fe(III) 盐，一种固体聚合全氟烷磺酸）在常规热和微波条件下。该方法中应用的微波和无溶剂条件缩短了反应时间，提高了产率并减少了副产物的形成。Strecker 反应与脂族仲胺在这些条件下也能顺利发生，这在常规条件下并不常见。 图形摘要
• A Mesoporous Indium Metal–Organic Framework: Remarkable Advances in Catalytic Activity for Strecker Reaction of Ketones
  作者：Daniel Reinares-Fisac、Lina María Aguirre-Díaz、Marta Iglesias、Natalia Snejko、Enrique Gutiérrez-Puebla、M. Ángeles Monge、Felipe Gándara

  DOI：10.1021/jacs.6b05706

  日期：2016.7.27

  porous, heterogeneous Lewis acid catalysts for multicomponent reactions, a new mesoporous metal-organic framework, InPF-110 ([In3O(btb)2(HCOO)(L)], (H3btb = 1,3,5-tris(4-carboxyphenyl)benzene acid, L = methanol, water, or ethanol), has been prepared with indium as the metal center. It exhibits a Langmuir surface area of 1470 m(2) g(-1), and its structure consists of hexagonal pores with a 2.8 nm aperture

  并且不需要加热或溶剂。此外，X 射线单晶衍射研究清楚地显示了通过与可接近的铟位点配位而发生的骨架-基材相互作用。
• Synthesis of 4-hydroxy-2(1H)-pyridones from azomethines and substituted dialkylmalonates
  作者：S. Kafka、T. Kappe

  DOI：10.1007/bf00806968

  日期：1997.10

  The reaction of azomethines 4 with substituted dialkyl malonates 5 leads to the formation of 3-substituted 4-hydroxy-2(1H)-pyridones 6 in moderate yields. The azomethines 4 are prepared via arylaminopropionitriles 3 or in the conventional way by acid catalyzed condensation of ketones 1 with anilines 2. Chlorination of pyridones 6 with sulfuryl chloride leads to compounds 8-10.