(E)-5,5'-bis-(4-bromo-phenyl)-[3,3']bifurylidene-2,2'-dione | 134949-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-5,5'-bis-(4-bromo-phenyl)-[3,3']bifurylidene-2,2'-dione
• 英文别名: (E)-5,5'-Bis-(4-brom-phenyl)-[3,3']bifuryliden-2,2'-dion；(3E)-5-(4-bromophenyl)-3-[5-(4-bromophenyl)-2-oxofuran-3-ylidene]furan-2-one
• CAS: 134949-94-3
• 化学式: C₂₀H₁₀Br₂O₄
• 分子量: 474.105
• InChiKey: YWKKINXZSQXCJU-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-5,5'-bis-(4-bromo-phenyl)-[3,3']bifurylidene-2,2'-dione 在 sodium acetate 作用下， 以 乙二醇 为溶剂， 生成 3,7-Bis-(4-bromo-phenyl)-pyrano[4,3-c]pyran-1,5-dione
  参考文献：
  名称：

  REARRANGEMENT OF SUBSTITUTED (E)-5,5?-DIPHENYLBIFURANYLIDENEDIONES TO 3,7-DIPHENYLPYRANO[4,3-c]PYRAN-1,5-DIONES

  摘要：

  The rate coefficients for the rearrangement of substituted (E)-5,5'-diphenylbifuranylidenediones to form the corresponding 3,7-diphenylpyrano[4,3-c]pyran-1,5-diones in ethane-1,2-diol at 30.0 degrees C, catalysed by sodium acetate, were determined, For the unsubstituted dione, the rate coefficients for there arrangement in various alcohols at 30.0 degrees C, and for three at 59.8 degrees C, were measured, The reactions were first order in both substrate and acetate anion, Rate coefficients were also measured for the catalysis of the rearrangement of the unsubstituted dione in ethanol and ethane-1,2-diol at 30.0 degrees C by a series of sodium meta/para-substituted benzoates, Bronsted-type correlations for the latter give alpha approximate to 1.2. Substrate substitutent effects on the rates of rearrangement of the diones were not marked, A good correlation was found between the rates of rearrangement of the unsubstituted dione and the solvent effect parameter E-T(30). This and other evidence indicated a probable mechanism involving a rapid pre-equilibrium between the substrate diones and the carboxylate anion, followed by the formation of an s-trans-enolate anion, The latter rotates to the s-cis isomer, which then intramolecularly attacks the second lactone ring, The process is then repeated with the product dione resulting from loss of the carboxylate anion. (C) 1997 by John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199704)10:4<191::aid-poc888>3.0.co;2-5
• 作为产物：
  描述：

  4-溴苯乙酮 在 sodium ethanolate 、 三溴化磷 、 甲苯 作用下， 生成 (E)-5,5'-bis-(4-bromo-phenyl)-[3,3']bifurylidene-2,2'-dione
  参考文献：
  名称：

  Chovin, Annales de Chimie (Cachan, France), 1938, vol. <11> 9, p. 447,491

  摘要：

  DOI：

文献信息

• Process for producing pechmann dye
  申请人：AMERICAN CYANAMID CO

  公开号：US02640836A1

  公开（公告）日：1953-06-02
• Bowden, Keith; Etemadi, Razieh; Ranson, Richard J., Journal of the Chemical Society. Perkin transactions II, 1991, # 5, p. 743 - 746
  作者：Bowden, Keith、Etemadi, Razieh、Ranson, Richard J.

  DOI：——

  日期：——
• Chovin, Annales de Chimie (Cachan, France), 1938, vol. <11> 9, p. 447,491
  作者：Chovin

  DOI：——

  日期：——
• REARRANGEMENT OF SUBSTITUTED (E)-5,5?-DIPHENYLBIFURANYLIDENEDIONES TO 3,7-DIPHENYLPYRANO[4,3-c]PYRAN-1,5-DIONES
  作者：Keith Bowden、Richard J. Ranson

  DOI：10.1002/(sici)1099-1395(199704)10:4<191::aid-poc888>3.0.co;2-5

  日期：1997.4

  The rate coefficients for the rearrangement of substituted (E)-5,5'-diphenylbifuranylidenediones to form the corresponding 3,7-diphenylpyrano[4,3-c]pyran-1,5-diones in ethane-1,2-diol at 30.0 degrees C, catalysed by sodium acetate, were determined, For the unsubstituted dione, the rate coefficients for there arrangement in various alcohols at 30.0 degrees C, and for three at 59.8 degrees C, were measured, The reactions were first order in both substrate and acetate anion, Rate coefficients were also measured for the catalysis of the rearrangement of the unsubstituted dione in ethanol and ethane-1,2-diol at 30.0 degrees C by a series of sodium meta/para-substituted benzoates, Bronsted-type correlations for the latter give alpha approximate to 1.2. Substrate substitutent effects on the rates of rearrangement of the diones were not marked, A good correlation was found between the rates of rearrangement of the unsubstituted dione and the solvent effect parameter E-T(30). This and other evidence indicated a probable mechanism involving a rapid pre-equilibrium between the substrate diones and the carboxylate anion, followed by the formation of an s-trans-enolate anion, The latter rotates to the s-cis isomer, which then intramolecularly attacks the second lactone ring, The process is then repeated with the product dione resulting from loss of the carboxylate anion. (C) 1997 by John Wiley & Sons, Ltd.