3-(2-硝基苯基)丙腈 | 114304-24-4

• 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: 3-(2-硝基苯基)丙腈
• 英文名称: 3-(2-nitrophenyl)propionitrile
• 英文别名: β-(2-Nitro-phenyl)-propionitril；3-(2-Nitrophenyl)propanenitrile
• CAS: 114304-24-4
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: NLELPJNIJLWQNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  3-(2-硝基苯基)丙腈 在 硫酸 作用下， 反应 4.5h， 以100%的产率得到3-(2-硝基苯基)丙酸
  参考文献：
  名称：

  5′-(2-Nitrophenylalkanoyl)-2′-deoxy-5-fluorouridines as potential prodrugs of FUDR for reductive activation

  摘要：

  Four 5'-(2-nitrophenylalkanoyl)-2'-deoxy-5-fluorouridines (1a-d) were designed and synthesized as potential prodrugs of FUDR for reductive activation. Two methyl groups were introduced alpha to the ester carbonyl to increase both the rate of cyclization activation and the stability of the conjugates towards serum esterases. Chemical reduction of the nitro group into an amino leads to cyclization and release of the active FUDR. Kinetic analysis of the cyclization activation process indicates that the two methyl groups alpha to the ester carbonyl restrict the rotational freedom of ground state molecule and promote the cyclization reaction. However, the two methyl groups also were found to render the conjugates as poor substrates of E. coli B nitroreductase. Conjugate 1c, without the two methyl groups, was reduced by E. coli B nitroreductase (t(1/2) = 8 h) to give two products, a N-hydroxyl lactam and the drug FUDR, suggesting that the enzymatic reduction and subsequent cyclization activation proceeded through the hydroxylamine intermediate. These results indicate that cyclization activation will occur once the nitro group is reduced either to an amino or to a hydroxylamino group. The fact that the amino intermediates cyclized easily to release the incorporated drug FUDR suggests the feasibility of using peptide-linked acyl 2-aminophenylalkanoic acid esters as potential prodrugs for proteolytic activation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00426-7
• 作为产物：
  描述：

  2-(2-硝基苯基)乙醇 在 吡啶 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 4.0h， 生成 3-(2-硝基苯基)丙腈
  参考文献：
  名称：

  5′-(2-Nitrophenylalkanoyl)-2′-deoxy-5-fluorouridines as potential prodrugs of FUDR for reductive activation

  摘要：

  Four 5'-(2-nitrophenylalkanoyl)-2'-deoxy-5-fluorouridines (1a-d) were designed and synthesized as potential prodrugs of FUDR for reductive activation. Two methyl groups were introduced alpha to the ester carbonyl to increase both the rate of cyclization activation and the stability of the conjugates towards serum esterases. Chemical reduction of the nitro group into an amino leads to cyclization and release of the active FUDR. Kinetic analysis of the cyclization activation process indicates that the two methyl groups alpha to the ester carbonyl restrict the rotational freedom of ground state molecule and promote the cyclization reaction. However, the two methyl groups also were found to render the conjugates as poor substrates of E. coli B nitroreductase. Conjugate 1c, without the two methyl groups, was reduced by E. coli B nitroreductase (t(1/2) = 8 h) to give two products, a N-hydroxyl lactam and the drug FUDR, suggesting that the enzymatic reduction and subsequent cyclization activation proceeded through the hydroxylamine intermediate. These results indicate that cyclization activation will occur once the nitro group is reduced either to an amino or to a hydroxylamino group. The fact that the amino intermediates cyclized easily to release the incorporated drug FUDR suggests the feasibility of using peptide-linked acyl 2-aminophenylalkanoic acid esters as potential prodrugs for proteolytic activation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00426-7

文献信息

• Jaenisch, Chemische Berichte, 1923, vol. 56, p. 2450
  作者：Jaenisch

  DOI：——

  日期：——
• Experiments on the <i>Chaperon</i> Effect in the Nitration of Aromatics
  作者：Paolo Strazzolini、Angelo G. Giumanini、Antonio Runcio、Massimo Scuccato

  DOI：10.1021/jo9709763

  日期：1998.2.1

  A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in alpha-position and a dilute solution of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced or tho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results mere compared with the corresponding classical nitration in H2SO4.
• US5628999A
  申请人：——

  公开号：US5628999A

  公开（公告）日：1997-05-13
• US5629319A
  申请人：——

  公开号：US5629319A

  公开（公告）日：1997-05-13
• US5681958A
  申请人：——

  公开号：US5681958A

  公开（公告）日：1997-10-28