2-(4-nitrobenzoyl)cyclohexanone | 38968-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-nitrobenzoyl)cyclohexanone
• 英文别名: 2-(4-nitrobenzoyl)cyclohexan-1-one
• CAS: 38968-78-4
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: JWCJFMMKJNFMGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  419.6±35.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-nitrobenzoyl)cyclohexanone 在 palladium on activated charcoal 氯化亚砜 、 水 、 氢气 、 sodium acetate 、 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 10.25h， 生成 7-<4-phenyl>heptanoic acid
  参考文献：
  名称：

  [EN] HYDROXAMIC ACID DERIVATIVES
  [FR] DÉRIVÉS D'ACIDE HYDROXAMIQUE

  摘要：

  公开号：

  WO2010085377A3
• 作为产物：
  描述：

  对硝基苯乙腈 在 vanadyl acetate 叔丁基过氧化氢 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(4-nitrobenzoyl)cyclohexanone
  参考文献：
  名称：

  [EN] HYDROXAMIC ACID DERIVATIVES
  [FR] DÉRIVÉS D'ACIDE HYDROXAMIQUE

  摘要：

  公开号：

  WO2010085377A3

文献信息

• Synthesis of Certain β-Diketones from Acid Chlorides and Ketones by Sodium Amide. Mono versus Diacylation of Sodio Ketones with Acid Chlorides¹
  作者：Bruce O. Linn、Charles R. Hauser

  DOI：10.1021/ja01604a032

  日期：1956.12
• High-Yielding Oxidation of β-Hydroxyketones to β-Diketones Using<i>o</i>-Iodoxybenzoic Acid
  作者：Samuel L. Bartlett、Christopher M. Beaudry

  DOI：10.1021/jo201810c

  日期：2011.12.2

  The oxidation of beta-hydroxyketones to beta-diketones was systematically investigated. o-Iodoxybenzoic add (IBX) was found to be efficient, operationally easy, and superior to other common oxidants. The reaction is suitable for milligram- to gram-scale oxidations.
• Suwinski, J.; Walczak, K., Polish Journal of Chemistry, 1992, vol. 66, # 5, p. 777 - 785
  作者：Suwinski, J.、Walczak, K.

  DOI：——

  日期：——
• Fos, Empar; Borras, Liset; Gasull, Maria, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 1, p. 203 - 208
  作者：Fos, Empar、Borras, Liset、Gasull, Maria、Mauleon, David、Carganico Germano

  DOI：——

  日期：——
• DNA-directed alkylating agents. 1. Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the reactivity of the mustard
  作者：Trudi A. Gourdie、Kisione K. Valu、G. Lance Gravatt、Theodore J. Boritzki、Bruce C. Baguley、Laurence P. G. Wakelin、William R. Wilson、Paul D. Woodgate、William A. Denny

  DOI：10.1021/jm00166a015

  日期：1990.4

  A series of DNA-targeted aniline mustards have been prepared, and their chemical reactivity and in vitro and in vivo cytotoxicity have been evaluated and compared with that of the corresponding simple aniline mustards. The alkylating groups were anchored to the DNA-intercalating 9-aminoacridine chromophore by an alkyl chain of fixed length attached at the mustard 4-position through a link group X, while the corresponding simple mustards possessed an electronically identical small group at this position. The link group was varied to provide a series of compounds of similar geometry but widely differing mustard reactivity. Variation in biological activity should then largely be a consequence of this varying reactivity. Rates of mustard hydrolysis in the two series related only to the electronic properties of the link group, with attachment of the intercalating chromophore having no effect. The cytotoxicities of the simple mustards correlated well with group electronic properties (with a 200-300-fold range in IC50S). The corresponding DNA-targeted mustards were much more potent (up to 100-fold), but their IC50 values varied much less with linker group electronic properties. Most of the DNA-targeted mustards showed in vivo antitumor activity, being both more active and more dose-potent than either the corresponding untargeted mustards and chlorambucil. These results show that targeting alkylating agents to DNA by attachment to DNA-affinic units may be a useful strategy.