[3-(bromomethyl)-3-(4-bromophenyl)oxiran-2-yl](4-bromophenyl)methanone | 27993-58-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3-(bromomethyl)-3-(4-bromophenyl)oxiran-2-yl](4-bromophenyl)methanone
• 英文别名: [3-bromomethyl-3-(4-bromo-phenyl)-oxiranyl]-(4-bromo-phenyl)-methanone
• CAS: 27993-58-4
• 化学式: C₁₆H₁₁Br₃O₂
• 分子量: 474.974
• InChiKey: KNAUGXVOLGNQMN-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C(Solv: ethanol (64-17-5))
• 沸点：
  524.0±50.0 °C(Predicted)
• 密度：
  1.895±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,4'-二溴苯乙酮 在 tetrabutylammonium hydrogen bifluoride 作用下， 以 四氢呋喃 为溶剂， 以33%的产率得到1-(4-溴苯基)-2-氟乙酮
  参考文献：
  名称：

  Electrophilic and nucleophilic side chain fluorination of para-substituted acetophenones

  摘要：

  para-Substituted alpha-fluoroacetophenones have been synthesised by three different routes. Electrophilic fluorination of trimethylsilyl enol ethers of acetophenones using Selectfluor (F-TEDA-BF4, 1-chloromethyl-4-fluoro- 1,4-diazoniabicyclo[ 2.2.2]octane bis-(tetrafluoroborate)) gave high to moderate yield depending on the electronic properties of the substituents. F-TEDA-BF4 mediated fluorination of acetophenones in methanol resulted in a mixture of alpha-fluoroacetophenones and the corresponding 2-fluoro- 1,1 -dimethyl acetals. The dimethyl acetals were hydrolysed using trifluoroacetic acid in water to maximise the yield of the product. Nucleophilic fluorination of alpha-bromoacetophenones using tetrabutylammoniurn hydrogen bifluoride (TBABF) led to moderate yield when having electron-donating substituents, whereas low yields were experienced when more electron-withdrawing substituents were introduced. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.060

文献信息

• Patil, Shivaraj P.; Kanawade, Shrikant B.; Shinde, Madhukar P., Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 1, p. 33 - 36
  作者：Patil, Shivaraj P.、Kanawade, Shrikant B.、Shinde, Madhukar P.、Toche, Raghunath B.

  DOI：——

  日期：——
• FORMATION OF OXIRANES DURING THE PREPARATION OF AROYLACETONITRILES
  作者：R. B. Toche、M. N. Jachak、N. S. Badgujar、A. B. Avhale、D. B. Kendre

  DOI：10.1080/00304940509354974

  日期：2005.8