2-(3-氯-4-硝基苯基)-2-苯基丙腈 | 55233-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3-氯-4-硝基苯基)-2-苯基丙腈
• 英文名称: 2-(3-Chloro-4-nitrophenyl)-2-phenylpropanenitrile
• CAS: 55233-09-5
• 化学式: C₁₅H₁₁ClN₂O₂
• 分子量: 286.718
• InChiKey: RSGBYXOGQWTBLD-UHFFFAOYSA-N

物化性质

• 熔点：
  50-51 °C(Solv: methanol (67-56-1))
• 沸点：
  184 °C(Press: 0.2 Torr)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-氯-4-硝基苯基)-2-苯基丙腈 在 盐酸 、 铁粉 作用下， 生成 2-(4-amino-3-chlorophenyl)-2-phenylpropanenitrile
  参考文献：
  名称：

  Makosza,M. et al., Roczniki Chemii, 1976, vol. 50, p. 1841 - 1858

  摘要：

  DOI：
• 作为产物：
  描述：

  硝基氯苯 、 α-甲基苯腈 在 potassium permanganate 、 sodium amide 作用下， 生成 2-(3-氯-4-硝基苯基)-2-苯基丙腈
  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。