1,4-bis(3-bromophenyl)butane-1,4-dione | 362047-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis(3-bromophenyl)butane-1,4-dione
• 英文别名: 1,4-di(3-bromophenyl)butanedione；1,4-bis-(3-bromophenyl)butanedione
• CAS: 362047-03-8
• 化学式: C₁₆H₁₂Br₂O₂
• 分子量: 396.078
• InChiKey: SZQOOZJLDPVUBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  500.1±45.0 °C(Predicted)
• 密度：
  1.611±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis(3-bromophenyl)butane-1,4-dione 在 lithium aluminium tetrahydride 、 硫酸 、 氢溴酸 、 乙酸酐 作用下， 以 四氢呋喃 、 乙醚 、 溶剂黄146 为溶剂， 生成 2,5-bis(3-bromophenyl)-3,4-dimethylfuran
  参考文献：
  名称：

  Discovery of new G-quadruplex binding chemotypes

  摘要：

  我们报告了一种新颖的基于呋喃的低分子量化学类型，具有高G-四链体亲和力和强效的抗增殖活性。

  DOI：

  10.1039/c3cc48616h
• 作为产物：
  描述：

  2,3-二溴苯乙酮 在 碘 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以51%的产率得到1,4-bis(3-bromophenyl)butane-1,4-dione
  参考文献：
  名称：

  One-Step Preparation of Symmetrical 1,4-Diketones from α-Halo Ketones in the Presence of Zn-I₂ as a Condensation Agent

  摘要：

  在 Zn-I2 作为缩合剂的作用下，11 种 1,4- 二苯基丁烷-1,4-二酮从相应的 δ-卤代苯乙酮一步制备得到，产率从中等到较高不等。该反应的机理途径可以用δ-卤代酮的类似于 Wurtz 的自缩合来解释。同样，3-氯戊烷-2,4-二酮也生成了 3,4-二乙酰基己烷-2,5-二酮，这是一种类似于 Wurtz 的缩合产物。

  DOI：

  10.1055/s-2004-829118

文献信息

• Visible-Light-Induced CS Bond Activation: Facile Access to 1,4-Diketones from β-Ketosulfones
  作者：Jun Xuan、Zhu-Jia Feng、Jia-Rong Chen、Liang-Qiu Lu、Wen-Jing Xiao

  DOI：10.1002/chem.201304898

  日期：2014.3.10

  A novel method for the synthesis of 1,4‐diketones from β‐ketosulfones was developed by means of a visible light‐induced CS bond activation process. Symmetrical and unsymmetrical 1,4‐diketones can be easily prepared in moderate to good yields.

  用于从β-1,4-酮砜二酮类合成的新方法是通过可见光诱导的C装置显影 S键激活过程。可以容易地制备对称和不对称的1,4-二酮，产量适中。
• Inhibition of the HIV-1 rev–RRE complex formation by unfused aromatic cations
  作者：G Xiao

  DOI：10.1016/s0968-0896(00)00344-8

  日期：2001.5

  RNA viruses cause a wide range of human diseases. Development of new agents to target such viruses is an active area of research. Towards this goal, a series of diphenylfuran cations as potential inhibitors of the Rev-RRE complex have been designed and synthesized. Analysis of the interaction of the diphenylfurans with RRE and TAR RNA model systems by gel shift assays indicates that they exhibit both sequence and structure-dependent binding modes. Our results show a strong interaction between the diphenylfuran ring system and RRE bases, while the TAR interactions are much weaker with the compounds that are the best inhibitors of Rev-RRE. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Structural Selectivity of Aromatic Diamidines
  作者：Jonathan B. Chaires、Jinsong Ren、Donald Hamelberg、Arvind Kumar、Vandna Pandya、David W. Boykin、W. David Wilson

  DOI：10.1021/jm049491e

  日期：2004.11.1

  Competition dialysis was used to study the interactions of 13 substituted aromatic diamidine compounds with 13 nucleic acid structures and sequences. The results show a striking selectivity of these compounds for the triplex structure poly dA:(poly dT)(2), a novel aspect of their interaction with nucleic acids not previously described. The triplex selectivity of selected compounds was confirmed by thermal denaturation studies. Triplex selectivity was found to be modulated by the location of amidine substiuents on the core phenyl-furan-phenyl ring scaffold. Molecular models were constructed to rationalize the triplex selectivity of DB359, the most selective compound in the series. Its triplex selectivity was found to arise from optimal ring stacking on base triplets, along with proper positioning of its amidine substituents to occupy the minor and the major-minor grooves of the triplex. New insights into the molecular recognition of nucleic acid structures emerged from these studies, adding to the list of available design principles for selectively targeting DNA and RNA.
• Discovery of new G-quadruplex binding chemotypes
  作者：Stephan A. Ohnmacht、Ehsan Varavipour、Rupesh Nanjunda、Ingrida Pazitna、Gloria Di Vita、Mekala Gunaratnam、Arvind Kumar、Mohamed A. Ismail、David W. Boykin、W. David Wilson、Stephen Neidle

  DOI：10.1039/c3cc48616h

  日期：——

  We report a novel furan-based low molecular weight chemotype with high G-quadruplex affinity and potent anti-proliferative activity.

  我们报告了一种新颖的基于呋喃的低分子量化学类型，具有高G-四链体亲和力和强效的抗增殖活性。
• One-Step Preparation of Symmetrical 1,4-Diketones from α-Halo Ketones in the Presence of Zn-I₂ as a Condensation Agent
  作者：Mustafa Ceylan、M. Gürdere、Yakup Budak、Cavit Kazaz、Hasan Seçen

  DOI：10.1055/s-2004-829118

  日期：——

  Eleven 1,4-diphenylbutane-1,4-diones have been prepared in one step from the corresponding α-halo acetophenones under the action of Zn-I2 as a condensation agent with moderate to high yields. The mechanistic pathway of the reaction can be explained by the Wurtz-like self-condensation of α-halo ketones. Similarly, 3-chloropentane-2,4-dione gave 3,4-diacetylhexane-2,5-dione, a Wurtz-like condensation product.

  在 Zn-I2 作为缩合剂的作用下，11 种 1,4- 二苯基丁烷-1,4-二酮从相应的 δ-卤代苯乙酮一步制备得到，产率从中等到较高不等。该反应的机理途径可以用δ-卤代酮的类似于 Wurtz 的自缩合来解释。同样，3-氯戊烷-2,4-二酮也生成了 3,4-二乙酰基己烷-2,5-二酮，这是一种类似于 Wurtz 的缩合产物。