5-羧基-2-硝基苯乙腈 | 104825-21-0

• 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: 5-羧基-2-硝基苯乙腈
• 中文别名: 5-羧基-2-硝基苄基氰化物
• 英文名称: (5-carboxy-2-nitrophenyl)acetonitrile
• 英文别名: 3-(Cyanomethyl)-4-nitrobenzoic acid
• CAS: 104825-21-0
• 化学式: C₉H₆N₂O₄
• 分子量: 206.158
• InChiKey: WSWMKJWDGKJFAO-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C
• 沸点：
  451.5±40.0 °C(Predicted)
• 密度：
  1.472±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  5-羧基-2-硝基苯乙腈 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 以64%的产率得到2-(5-carboxy-2-nitrophenyl)acetic acid
  参考文献：
  名称：

  The α,5-Dicarboxy-2-nitrobenzyl Caging Group, a Tool for Biophysical Applications with Improved Hydrophilicity: Synthesis, Photochemical Properties and Biological Characterization

  摘要：

  AbstractEarlier we reported on the synthesis of α,4‐dicarboxy‐2‐nitrobenyzl caged compounds (Schaper, K. et al. [2002] Eur. J. Org. Chem., 1037–1046). These compounds have the advantage of an increased hydrophilicity compared with the well‐established α‐carboxy‐2‐nitrobenzyl caged compounds; however, the release of the active compound becomes slower due to the introduction of the additional carboxy group. Based upon theoretical calculations we predicted that the release would become faster when the additional carboxy group is moved to the 5‐position. Here we describe the synthesis and the photochemical and biological characterization of an α,5‐dicarboxy‐2‐nitrobenyzl caged compound. The high hydrophilicity of the new caging group is maintained due to the fact that the additional carboxy moiety is preserved, while the release of the active species from the new derivative is even faster than for the reference, an α‐CNB caged compound.

  DOI：

  10.1111/j.1751-1097.2010.00803.x
• 作为产物：
  描述：

  苯基腈乙基硫醚 、 对硝基苯甲酸 在 sodium hydroxide 作用下， 生成 5-羧基-2-硝基苯乙腈
  参考文献：
  名称：

  Vicarious Nucleophilic Substitution of Hydrogen in Nitrobenzoic Acids

  摘要：

  对三种异构体硝基苯甲酸2-4中的氢进行的间接亲核取代反应进行了研究。带负电的羧酸根阴离子取代基并未干扰反应过程，反应以良好到中等的收率生成产物6和7。

  DOI：

  10.1055/s-1986-33420

文献信息

• Vicarious Nucleophilic Substitution of Hydrogen in Nitrobenzoic Acids
  作者：M. Makosza、S. Ludwiczak

  DOI：10.1055/s-1986-33420

  日期：——

  The vicarious nucleophilic substitution of hydrogen in three isomeric nitrobenzoic acids 2-4 was studied. The negatively charged carboxylate anion substituent does not disturb the reaction course which proceeds with good to moderate yields to give products 6 and 7.

  对三种异构体硝基苯甲酸2-4中的氢进行的间接亲核取代反应进行了研究。带负电的羧酸根阴离子取代基并未干扰反应过程，反应以良好到中等的收率生成产物6和7。
• MAKOSZA, M.;LUDWICZAK, S., SYNTHESIS, BRD, 1986, N 1, 50-52
  作者：MAKOSZA, M.、LUDWICZAK, S.

  DOI：——

  日期：——
• The α,5-Dicarboxy-2-nitrobenzyl Caging Group, a Tool for Biophysical Applications with Improved Hydrophilicity: Synthesis, Photochemical Properties and Biological Characterization
  作者：Klaus Schaper、Sayed Abdollah Madani Mobarekeh、Peter Doro、Daniela Maydt

  DOI：10.1111/j.1751-1097.2010.00803.x

  日期：2010.11

  AbstractEarlier we reported on the synthesis of α,4‐dicarboxy‐2‐nitrobenyzl caged compounds (Schaper, K. et al. [2002] Eur. J. Org. Chem., 1037–1046). These compounds have the advantage of an increased hydrophilicity compared with the well‐established α‐carboxy‐2‐nitrobenzyl caged compounds; however, the release of the active compound becomes slower due to the introduction of the additional carboxy group. Based upon theoretical calculations we predicted that the release would become faster when the additional carboxy group is moved to the 5‐position. Here we describe the synthesis and the photochemical and biological characterization of an α,5‐dicarboxy‐2‐nitrobenyzl caged compound. The high hydrophilicity of the new caging group is maintained due to the fact that the additional carboxy moiety is preserved, while the release of the active species from the new derivative is even faster than for the reference, an α‐CNB caged compound.