3-溴-4'-氯二苯甲酮 | 75762-56-0

• 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: 3-溴-4'-氯二苯甲酮
• 英文名称: (3-bromophenyl)-(4-chlorophenyl)methanone
• 英文别名: (4-chlorophenyl)(3-bromophenyl)methanone；3-bromo-4′-chlorobenzophenone；3-bromo-4'-chlorobenzophenone
• CAS: 75762-56-0
• 化学式: C₁₃H₈BrClO
• 分子量: 295.563
• InChiKey: JDSRHMLEPCMXHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  3-溴-4'-氯二苯甲酮 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 生成 1-bromo-3-(4-chlorobenzyl)benzene
  参考文献：
  名称：

  Blackwell,J.; Hickinbottom,W.J., Journal of the Chemical Society, 1961, p. 1405 - 1407

  摘要：

  DOI：
• 作为产物：
  描述：

  间溴苯甲酸 在 aluminum (III) chloride 、 氯化亚砜 作用下， 生成 3-溴-4'-氯二苯甲酮
  参考文献：
  名称：

  Analogues of Fenarimol Are Potent Inhibitors of Trypanosoma cruzi and Are Efficacious in a Murine Model of Chagas Disease

  摘要：

  We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC(50)s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.

  DOI：

  10.1021/jm2015809

文献信息

• Palladium(II)-Catalyzed Desulfitative Synthesis of Aryl Ketones from Sodium Arylsulfinates and Nitriles: Scope, Limitations, and Mechanistic Studies
  作者：Bobo Skillinghaug、Christian Sköld、Jonas Rydfjord、Fredrik Svensson、Malte Behrends、Jonas Sävmarker、Per J. R. Sjöberg、Mats Larhed

  DOI：10.1021/jo501875n

  日期：2014.12.19

  The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The

  已经开发了一种快速有效的方案，在受控的微波辐射下，钯（II）催化从芳基亚磺酸钠和各种有机腈生产芳基酮。通过结合14个芳基亚磺酸钠和21个腈给出55个芳基酮实例，证明了该反应的广泛范围。另一个实例说明，通过选择腈反应物，苯并呋喃也是可得到的。通过电喷雾电离质谱和DFT计算研究了反应机理。还比较了从腈的脱硫合成芳基酮与从苯甲酸开始的相应转化。能量分布图的比较表明，2的脱羧所需的自由能 6-二甲氧基苯甲酸，尤其是苯甲酸比用于生成关键的芳基钯中间体的相应的脱硫方法要高。通过ESI-MS和DFT计算检测到的钯（II）中间体对催化循环提供了详细的了解。
• Design, synthesis, and biological evaluation of potent thiosemicarbazone based cathepsin L inhibitors
  作者：G.D. Kishore Kumar、Gustavo E. Chavarria、Amanda K. Charlton-Sevcik、Wara M. Arispe、Matthew T. MacDonough、Tracy E. Strecker、Shen-En Chen、Bronwyn G. Siim、David J. Chaplin、Mary Lynn Trawick、Kevin G. Pinney

  DOI：10.1016/j.bmcl.2009.12.090

  日期：2010.2

  A small library of 36 functionalized benzophenone thiosemicarbazone analogs has been prepared by chemical synthesis and evaluated for their ability to inhibit the cysteine proteases cathepsin L and cathepsin B. Inhibitors of cathepsins L and B have the potential to limit or arrest cancer metastasis. The six most active inhibitors of cathepsin L (IC50 < 85 nM) in this series incorporate a meta-bromo sub-stituent in one aryl ring along with a variety of functional groups in the second aryl ring. These six analogs are selective for their inhibition of cathepsin L versus cathepsin B (IC50 > 10,000 nM). The most active analog in the series, 3-bromophenyl-2'-fluorophenyl thiosemicarbazone 1, also efficiently inhibits cell invasion of the DU-145 human prostate cancer cell line. (C) 2010 Elsevier Ltd. All rights reserved.
• Aromatic compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0085959B1

  公开（公告）日：1989-04-19
• Verfahren zur Herstellung von symmetrischen Diarylacetylenen
  申请人：BAYER AG

  公开号：EP0425930B1

  公开（公告）日：1994-09-28
• US4120687A
  申请人：——

  公开号：US4120687A

  公开（公告）日：1978-10-17