2-硝基-5-氰基苯乙酮 | 180343-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-硝基-5-氰基苯乙酮
• 英文名称: 2-nitro-5-cyanoacetophenone
• 英文别名: 3-acetyl-4-nitro-benzonitrile；4-Nitro-3-acetyl-benzoesaeure-nitril；3-Acetyl-4-nitro-benzonitril；3-Acetyl-4-nitrobenzonitrile；3-acetyl-4-nitrobenzonitrile
• CAS: 180343-61-7
• 化学式: C₉H₆N₂O₃
• 分子量: 190.158
• InChiKey: HCAVDAAVEPZNCW-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  382.0±32.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-硝基-5-氰基苯乙酮 在 盐酸 、 tin 作用下， 生成 3-乙酰基-4-氨基苯甲腈
  参考文献：
  名称：

  Substituent Effects on the Lifetimes and Reactivities of Arylnitrenium Ions Studied by Laser Flash Photolysis and Photothermal Beam Deflection

  摘要：

  Photolysis of 5-substituted-N-tert-butyl-3-methylanthranilium produces transient N-tert-butyl-(2-acetyl-4-substituted) phenylnitrenium ions. This is confirmed by identification of the stable products, transient absorption experiments, and photothermal beam deflection experiments. Analysis of the stable photoproducts shows that the major decay pathway for these species is addition of nucleophiles to the aromatic ring. The kinetics of the these reactions were examined with the goal of determining how various ring substituents affect arylnitrenium ion stability. Rate constants measured for the 4-phenyl and 4-methoxy derivatives are compared with those from previous work. It is shown that a 4-phenyl group stabilizes the nitrenium ion to approximately the same extent as a 4-methoxy group. Both of these substituents stabilize the arylnitrenium ions considerably more than 4-halogens or a 4-methyl group. Time resolved photothermal beam deflection experiments were applied to the 4-cyano and 4-unsubstituted derivatives, which gave no transient absorption spectra. The latter two compounds are shown to have lifetimes of less than 100 ns.

  DOI：

  10.1021/ja961518z
• 作为产物：
  描述：

  3-乙酰胺基苯乙酮 在 盐酸 、 硫酸 、 硝酸 、 溶剂黄146 、 copper(l) chloride 作用下， 生成 2-硝基-5-氰基苯乙酮
  参考文献：
  名称：

  Simpson et al., Journal of the Chemical Society, 1945, p. 646,655

  摘要：

  DOI：

文献信息

• Design, synthesis, and SAR of substituted acrylamides as factor Xa inhibitors
  作者：Yonghong Song、Lane Clizbe、Chhaya Bhakta、Willy Teng、Wenhao Li、Yanhong Wu、Zhaozhong Jon Jia、Penglie Zhang、Lingyan Wang、Brandon Doughan、Ting Su、James Kanter、John Woolfrey、Paul Wong、Brian Huang、Katherine Tran、Uma Sinha、Gary Park、Andrea Reed、John Malinowski、Stan Hollenbach、Robert M. Scarborough、Bing-Yan Zhu

  DOI：10.1016/s0960-894x(02)00199-3

  日期：2002.6

  Substituted acrylamides were used as templates that bridge P1 and P4 binding elements, resulting in a series of potent sub-nanomolar) and selective factor Xa inhibitors. In this template, cis-geometry of P1 and P4 ligands is highly preferred. SAR on the substituting groups, as well as on modification of P1 and P4 moieties is described. Compounds in this series show good in vivo efficacy in animal models. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Simpson et al., Journal of the Chemical Society, 1945, p. 646,655
  作者：Simpson et al.

  DOI：——

  日期：——
• Substituent Effects on the Lifetimes and Reactivities of Arylnitrenium Ions Studied by Laser Flash Photolysis and Photothermal Beam Deflection
  作者：Rebecca J. Robbins、David M. Laman、Daniel E. Falvey

  DOI：10.1021/ja961518z

  日期：1996.1.1

  Photolysis of 5-substituted-N-tert-butyl-3-methylanthranilium produces transient N-tert-butyl-(2-acetyl-4-substituted) phenylnitrenium ions. This is confirmed by identification of the stable products, transient absorption experiments, and photothermal beam deflection experiments. Analysis of the stable photoproducts shows that the major decay pathway for these species is addition of nucleophiles to the aromatic ring. The kinetics of the these reactions were examined with the goal of determining how various ring substituents affect arylnitrenium ion stability. Rate constants measured for the 4-phenyl and 4-methoxy derivatives are compared with those from previous work. It is shown that a 4-phenyl group stabilizes the nitrenium ion to approximately the same extent as a 4-methoxy group. Both of these substituents stabilize the arylnitrenium ions considerably more than 4-halogens or a 4-methyl group. Time resolved photothermal beam deflection experiments were applied to the 4-cyano and 4-unsubstituted derivatives, which gave no transient absorption spectra. The latter two compounds are shown to have lifetimes of less than 100 ns.