4-氰基-3-硝基吡啶 | 103698-09-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 4-氰基-3-硝基吡啶
• 中文别名: 3-硝基异烟腈
• 英文名称: 4-cyano-3-nitropyridine
• 英文别名: 3-Nitroisonicotinonitrile；3-nitropyridine-4-carbonitrile
• CAS: 103698-09-5
• 化学式: C₆H₃N₃O₂
• 分子量: 149.109
• InChiKey: WQSGWOANQDEUHL-UHFFFAOYSA-N

物化性质

• 沸点：
  309.6±27.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-氰基-3-硝基吡啶 在 palladium on activated charcoal 盐酸 、 氢气 、 双氧水 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、500.0 kPa 条件下， 反应 5.5h， 生成 3-氨基-2-氯-异烟腈
  参考文献：
  名称：

  制备4-取代的3-氨基-2-氯吡啶，合成奈韦拉平类似物

  摘要：

  开发了一种新的制备3-氨基-2-氯吡啶的新方法，该3-氨基-2-氯吡啶在4-位具有取代基（甲基，苯基，羧酰胺，甲氧基羰基，乙酰基，苯甲酰基和氰基）。逆转录酶抑制剂奈韦拉平的异喹啉类似物是由4-氨基-3-氯异喹啉合成的。

  DOI：

  10.1002/jhet.5570380114
• 作为产物：
  描述：

  4-氰基吡啶 在 五氧化二氮 、 sodium hydrogensulfite 作用下， 生成 4-氰基-3-硝基吡啶
  参考文献：
  名称：

  The Synthesis of beta-Nitropyridine Compounds.

  摘要：

  Pyridine and a number of substituted pyridines have been nitrated by reaction with N2O5 followed by reaction with an aqueous solution of SO(2)xH(2)O or NaHSO3. The dependence of the yields on the pH of the aqueous reaction medium, on the concentration of SO(2)xH(2)O-HSO3-, on addition of methanal to the aqueous phase, and on the reaction temperature were investigated. The yields obtained with NaHSO3 were: 3-nitropyridine 77%, 2-methyl-5-nitropyridine 36%, 3-methyl-5-nitropyridine 24%, 3-acetyl-5-nitropyridine 18%, 5-nitropyridine-3-carboxylic acid 15%, 3-chloro-5-nitropyridine 11%, 4-methyl-3-nitropyridine 39%, 4-acetyl-3-nitropyridine 67%, 4-cyano-3-nitropyridine 45%, 4-phenyl-3-nitropyridine 68%, 4-formyl-3-nitropyridine 62% (from reaction in liquid SO2), 3-nitropyridine-4-carboxylic acid 48%, methyl 3-nitropyridine-4-carboxylate 75%, 2,3-dimethyl-5-nitropyridine 37%, 2,4-dimethyl-5-nitropyridine 64%, 3-nitroquinoline 10% and 4-nitroisoquinoline 42%.

  DOI：

  10.3891/acta.chem.scand.53-0141

文献信息

• The oxidative amination of 3-nitropyridines
  作者：Jan M Bakke、Harald Svensen

  DOI：10.1016/s0040-4039(01)00724-9

  日期：2001.6

  3-Nitropyridine was reacted with ammonia or alkylamines and KMnO4 under several different conditions. Substitutions in the pura posit ion to the nitro group were obtained with high regio selectivity: with ammonia, 2-amino-5-nitropyridine (66%), with butylamine, 2-butylamino-5-nitropyridine (92%), with diethylamine, 2-diethylamino-5-nitropyridine (49%). Under the same conditions, with methyl-3-nitroisonicotinoate and diethylamine/KMnO4, methyl 2-diethylamino-5-nitroisonicotinoate (48%), with 4-acetyl-3-nitropyridine (protected by ethylene glycol) 2-diethylamino-4-acetyl-5-nitropyridine (72%, protected) and with 4-cyano-3-nitropyridine, 2-amino-4-cyano-5-nitropyridine (41%) were obtained. All yields are isolated. (C) 2001 Elsevier Science Ltd. All rights reserved.