3-phenyl-4-bromo-5H-furan-2-one | 178619-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-phenyl-4-bromo-5H-furan-2-one
• 英文别名: 4-bromo-3-phenyl-2(5H)-furanone；3-bromo-4-phenyl-2H-furan-5-one
• CAS: 178619-02-8
• 化学式: C₁₀H₇BrO₂
• 分子量: 239.068
• InChiKey: KVWOPBVARGZMOS-UHFFFAOYSA-N

物化性质

• 沸点：
  380.6±42.0 °C(Predicted)
• 密度：
  1.659±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-4-bromo-5H-furan-2-one 在 sodium azide 作用下， 以 甲醇 为溶剂， 反应 21.0h， 以84%的产率得到4-azido-3-phenyl-5H-furan-2-one
  参考文献：
  名称：

  4-Azidotetronic Acids: A New Class of Azido Derivatives

  摘要：

  4-Azidotetronic derivatives bearing different substituent groups on the carbon atom in position 3 were easily obtained by reaction of the corresponding 4-bromotetronic compounds with sodium azide in methanol at room temperature.

  DOI：

  10.1080/00397910008087364
• 作为产物：
  描述：

  4-羟基-3-苯基-2(5H)-呋喃酮 在 草酰溴 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到3-phenyl-4-bromo-5H-furan-2-one
  参考文献：
  名称：

  4-Azidotetronic Acids: A New Class of Azido Derivatives

  摘要：

  4-Azidotetronic derivatives bearing different substituent groups on the carbon atom in position 3 were easily obtained by reaction of the corresponding 4-bromotetronic compounds with sodium azide in methanol at room temperature.

  DOI：

  10.1080/00397910008087364

文献信息

• [EN] PROCESS FOR MAKING PHENYL HETEROCYCLES USEFUL AS COX-2 INHIBITORS<br/>[FR] PROCEDE DE PRODUCTION D'HETEROCYCLES PHENYLIQUES UTILES COMME INHIBITEURS DE COX-2
  申请人：MERCK & CO., INC.

  公开号：WO1996008482A1

  公开（公告）日：1996-03-21

  (EN) The invention encompasses a process for making compounds of formula (I) useful in the treatment of cyclooxygenase-2 mediated diseases.(FR) Procédé de production de composés de formule (I) utiles dans le traitement de maladies cyclooxygénase-2-dépendantes.

  该发明涉及一种用于制备式(I)化合物的方法，该化合物可用于治疗环氧化酶-2介导的疾病。
• Silver Ion-assisted Solvolysis of 2,2-Dibromo-1-phenylcyclopropanecarboxylic Acid: Solvent-dependent Competition between Decarboxylation and Ring Closure.
  作者：Leiv K. Sydnes、Rajesh Mungaroo、John S. Svendsen、Jacek Stawinski

  DOI：10.3891/acta.chem.scand.52-1392

  日期：——

  The solvolysis of the title compound has been studied in several alcohols (methanol, 2,2,2-trifluoroethanol, isopropyl alcohol, tert-butyl alcohol and 1,I,1,3,3,3-hexafluoro-2-propanol [HFP]) in the presence of an excess of sliver trifluoroacetate. In all solvents the corresponding butenolide, 4-bromo-3-phenyl-2(SH)-furanone, was a major or the predominant product. Another product formed in all solvents but HFP was (Z)-4-alkoxy-3-bromo-2-phenyl-2-butenoic acid, which resulted from solvent attack on intermediate allylic cations. Furthermore, both 3-alkoxy-1-phenyl-1-propyne and 3-alkoxy-1-phenyl-1-propanone were formed except when reactions were performed in HFP; their formation involved decarboxylation and their total yield was 15-40%.
• 4-Azidotetronic Acids: A New Class of Azido Derivatives
  作者：E. M. Beccalli、E. Erba、P. Trimarco

  DOI：10.1080/00397910008087364

  日期：2000.2

  4-Azidotetronic derivatives bearing different substituent groups on the carbon atom in position 3 were easily obtained by reaction of the corresponding 4-bromotetronic compounds with sodium azide in methanol at room temperature.