1,4-bis(3,5-difluorophenyl)-1,4-butanedione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis(3,5-difluorophenyl)-1,4-butanedione
• 英文别名: 1,4-bis(3,5-difluorophenyl)butane-1,4-dione
• 化学式: C₁₆H₁₀F₄O₂
• 分子量: 310.248
• InChiKey: UUXUIWOPZVTBAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 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：
  6

反应信息

• 作为反应物：
  描述：

  烯丙苯 、 1,4-bis(3,5-difluorophenyl)-1,4-butanedione 在 二氯二茂锆 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 8.0h， 以53%的产率得到anti-1,4-bis(3,5-difluorophenyl)-5-phenyl-6-heptene-1,4-diol
  参考文献：
  名称：

  Transformation of Zirconocene−Olefin Complexes into Zirconocene Allyl Hydride and Their Use as Dual Nucleophilic Reagents:  Reactions with Acid Chloride and 1,4-Diketone

  摘要：

  Zirconocene-olefin complexes Cp2Zr(H2C=CHR), prepared in benzene-THF at 0 degreesC, react with acid chlorides to provide homoallylic alcohols. The key is an equilibrium between the zirconocene-olefin complexes and the corresponding zirconocene allyl hydride complexes via allylic C-H bond cleavage of the coordinating alkenes. Furthermore, the zirconocene-olefin complexes are also available for the reaction with 1,4-diketone to afford anti-1,4-diols with excellent diastereoselectivity. Thus, Cp2Zr(H2C CHR) serves as a donor of both hydride and an allylic group. These reactions also proceed efficiently by using zirconocene-olefin complexes, derived from Cp2ZrCl2, Mg metal, and 1-alkenes.

  DOI：

  10.1021/ja049184y
• 作为产物：
  描述：

  1-(3,5-difluorophenyl)-2-(phenylsulfonyl)ethanone 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 potassium carbonate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以65%的产率得到1,4-bis(3,5-difluorophenyl)-1,4-butanedione
  参考文献：
  名称：

  可见光诱导的C ？S键活化：轻松获得β-酮砜中的1,4-二酮

  摘要：

  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。

  DOI：

  10.1002/chem.201304898

文献信息

• Highly Diastereoselective Tandem Reduction–Allylation Reactions of 1,4-Diketones with Zirconocene–Olefin Complexes
  作者：Kazuya Fujita、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1002/anie.200351480

  日期：2003.6.6
• Transformation of Zirconocene−Olefin Complexes into Zirconocene Allyl Hydride and Their Use as Dual Nucleophilic Reagents:  Reactions with Acid Chloride and 1,4-Diketone
  作者：Kazuya Fujita、Hideki Yorimitsu、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/ja049184y

  日期：2004.6.1

  Zirconocene-olefin complexes Cp2Zr(H2C=CHR), prepared in benzene-THF at 0 degreesC, react with acid chlorides to provide homoallylic alcohols. The key is an equilibrium between the zirconocene-olefin complexes and the corresponding zirconocene allyl hydride complexes via allylic C-H bond cleavage of the coordinating alkenes. Furthermore, the zirconocene-olefin complexes are also available for the reaction with 1,4-diketone to afford anti-1,4-diols with excellent diastereoselectivity. Thus, Cp2Zr(H2C CHR) serves as a donor of both hydride and an allylic group. These reactions also proceed efficiently by using zirconocene-olefin complexes, derived from Cp2ZrCl2, Mg metal, and 1-alkenes.
• 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。