2-bromo-1-(4,5-dihydrofuran-3-yl)-2,2-difluoroethanone | 1087792-68-4

• 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: 2-bromo-1-(4,5-dihydrofuran-3-yl)-2,2-difluoroethanone
• 英文别名: 2-Bromo-1-(4,5-dihydrofuran-3-yl)-2,2-difluoroethan-1-one；2-bromo-1-(2,3-dihydrofuran-4-yl)-2,2-difluoroethanone
• CAS: 1087792-68-4
• 化学式: C₆H₅BrF₂O₂
• mdl: MFCD11099669
• 分子量: 227.005
• InChiKey: UDLVKGRNMLFELF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(4,5-dihydrofuran-3-yl)-2,2-difluoroethanone 、 4-甲苯硫酚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 以75%的产率得到1-(4,5-dihydrofuran-3-yl)-2,2-difluoro-2-(p-tolylthio)ethanone
  参考文献：
  名称：

  Synthesis and substitution reactions of β-alkoxyvinyl bromodifluoromethyl ketones

  摘要：

  beta-Alkoxyvinyl bromodifluoromethyl ketones 1a, 1b and 1c were synthesized by the reaction of bromodifluoroacetic anhydride with appropriate vinyl ethers in high yields. The acyclic enone 1a reacted with amines to give the corresponding beta-aminovinyl bromodifluoromethyl ketones 2 in good yields. The reaction of la with electrophilic reagent ICI yielded alpha-iodoenone 4. The substitution reaction of the cyclic enones 1b and 1c with thio-nucleophiles gave the corresponding difluoromethylene thioethers 6. The three-component reactions of 2 with primary amines and formaldehyde gave multifunctional 1,2,3,4-tetrahydropyrimidine 3 in moderate yields. (c) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.09.001
• 作为产物：
  描述：

  2,3-二氢呋喃 、 溴二氟乙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2-bromo-1-(4,5-dihydrofuran-3-yl)-2,2-difluoroethanone
  参考文献：
  名称：

  Synthesis and substitution reactions of β-alkoxyvinyl bromodifluoromethyl ketones

  摘要：

  beta-Alkoxyvinyl bromodifluoromethyl ketones 1a, 1b and 1c were synthesized by the reaction of bromodifluoroacetic anhydride with appropriate vinyl ethers in high yields. The acyclic enone 1a reacted with amines to give the corresponding beta-aminovinyl bromodifluoromethyl ketones 2 in good yields. The reaction of la with electrophilic reagent ICI yielded alpha-iodoenone 4. The substitution reaction of the cyclic enones 1b and 1c with thio-nucleophiles gave the corresponding difluoromethylene thioethers 6. The three-component reactions of 2 with primary amines and formaldehyde gave multifunctional 1,2,3,4-tetrahydropyrimidine 3 in moderate yields. (c) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.09.001