2-Phenyl-2-(2-chlor-4-nitro-phenyl)-propionitril | 22156-88-3

• 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: 2-Phenyl-2-(2-chlor-4-nitro-phenyl)-propionitril
• CAS: 22156-88-3
• 化学式: C₁₅H₁₁ClN₂O₂
• 分子量: 286.718
• InChiKey: RZSVBIDGCOVEQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  α-甲基苯腈 在 三甲基氯硅烷 、 potassium tert-butylate 作用下， 反应 0.03h， 生成 2-Phenyl-2-(2-chlor-4-nitro-phenyl)-propionitril
  参考文献：
  名称：

  Oxidative Nucleophilic Substitution of Hydrogen in Nitroarenes

  摘要：

  AbstractCarbanions of 2‐phenylpropionitrile were found to add to nitroarenes in liquid ammonia to form σH adducts, which were oxidized with KMnO4 to yield products of oxidative nucleophilic substitution of hydrogen (ONSH) in the position para to the nitro group. Treatment of the carbanion‐nitroarene system with methyl iodide at ‐70°C indicated that the addition proceeds almost to completion. Thus, for the first time, the persistence of σH adducts, formed between free anions and mononitroarenes, has been demonstrated. It was also shown that KMnO4 oxidizes σH adducts to nitrobenzene faster than it does carbanions. This selective ONSH in the para positions of nitroarenes is a general process. However, some substituents hinder or inhibit the oxidation step.

  DOI：

  10.1002/chem.19970031217

文献信息

• Reactions of organic anions—L
  作者：M. Makosza、M. Jagusztyn-Grochowska、M. Ludwikow、M. Jawdosiuk

  DOI：10.1016/s0040-4020(01)90658-1

  日期：1974.1

  Reaction of phenylalkanenitriles and diphenylacetonitrile with aromatic nitro compounds were studied using various base-solvent systems. Four independent types of reaction: substitution of halogen, substitution of nitro group, substitution of hydride anion and electron transfer were observed. Relationship—reaction pathway—conditions have been discussed.

  使用各种碱溶剂系统研究了苯基链烯腈和二苯乙腈与芳族硝基化合物的反应。观察到四种独立的反应类型：卤素取代，硝基取代，氢化物阴离子取代和电子转移。关系-反应途径-条件已经讨论过。
• DMD Oxidation of <b><i>in-Situ</i></b>-Generated σ^H Adducts Derived from Nitroarenes and the Carbanion of 2-Phenylpropionitrile to Phenols:  The First Direct Substitution of a Nitro by a Hydroxy Group
  作者：Waldemar Adam、Mieczysław Ma̧kosza、Krzysztof Staliński、Cong-Gui Zhao

  DOI：10.1021/jo980173v

  日期：1998.6.1

  The dimethyldioxirane (DMD) oxidation of sigma(H) adducts derived from nitroarenes and the carbanion of 2-phenylpropionitrile yields unexpectedly the phenols 5 as the major products, while the usually observed nitroarenes 4 are formed in very little amounts, if any. The phenol yield was much improved when a small quantity (0.5-1.0 equiv.) of water was added at the start of the reaction. This novel oxidation of Meisenheimer complexes provides the first direct synthesis of phenols from nitroarenes, an unprecendented transformation.