4-bromo-3,5-dimethyl-2(5H)-furanone | 121900-64-9

• 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: 4-bromo-3,5-dimethyl-2(5H)-furanone
• 英文别名: 3-bromo-2,4-dimethyl-2H-furan-5-one
• CAS: 121900-64-9
• 化学式: C₆H₇BrO₂
• 分子量: 191.024
• InChiKey: DWNKGEFEQDNOFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  0
• 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：
  2

反应信息

• 作为产物：
  描述：

  ethyl 2-methylpenta-2,3-dienoate 在 copper(ll) bromide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以72%的产率得到4-bromo-3,5-dimethyl-2(5H)-furanone
  参考文献：
  名称：

  CuBr2-mediated direct aqueous bromolactonization of 2,3-allenoates. An efficient access to β-bromobutenolides

  摘要：

  An efficient procedure for the synthesis of beta -bromobutenolides was developed. 2,3-Allenoates with different substitution patterns react with CuBr2 in aqueous ethanol at 80-85 degreesC to afford the corresponding beta -bromobutenolides in moderate to excellent yields (up to 97%). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00634-7

文献信息

• Hemmingsen, Tor H.; Svendsen, John S.; Sydnes, Leiv K., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1988, vol. 42, # 10, p. 651 - 661
  作者：Hemmingsen, Tor H.、Svendsen, John S.、Sydnes, Leiv K.

  DOI：——

  日期：——
• Silver Ion-assisted Solvolysis of trans-2,2-Dibromo-1,3-dimethylcyclopropanecarboxylic Acid: Selective Formation of 4-Bromo-3,5-dimethyl-2(5H)-furanone.
  作者：Leiv K. Sydnes、Rajesh Mungaroo、Berit A. Aanesen、Jacek Stawinski

  DOI：10.3891/acta.chem.scand.52-1386

  日期：——

  The title compound has been solvolysed in 2,2,2-trifluoroethanol (IFE), isopropyl alcohol (IPA), 1,1,1,3,3,3-hexafluoro-2-propanol (HFP) and tert-butyl alcohol (TBA) in the presence of silver trifluoroacetate. The product distribution is sensitive to the solvent used. In TFE and IPA two major products were formed, the butenolide 4-bromo-3,5-dimethyl-2 (SH)-furanone and the corresponding (Z)-4-alkoxy-3-bromo-2-methyl-2-pentenoic acid, but, in addition, minor amounts of 2-alkoxy-3-bromo-2-methyl-3-pentenoic acid and 3-bromo-2-hydroxy-2-methyl-3-pentenoic acid were also obtained. In HFP and TEA the furanone was formed in better than 80% yield, the other products being 3-bromo-2-hydroxy-2-methyl-3-pentenoic acid and 3-bromo-2-methyl-2,4-pentadienoic acid. The outcome of the reactions is discussed on the basis of the nucleophilicity, the hydrogen-bonding ability and the polarity of the solvents.
• CuBr2-mediated direct aqueous bromolactonization of 2,3-allenoates. An efficient access to β-bromobutenolides
  作者：Shengming Ma、Shulin Wu

  DOI：10.1016/s0040-4039(01)00634-7

  日期：2001.6

  An efficient procedure for the synthesis of beta -bromobutenolides was developed. 2,3-Allenoates with different substitution patterns react with CuBr2 in aqueous ethanol at 80-85 degreesC to afford the corresponding beta -bromobutenolides in moderate to excellent yields (up to 97%). (C) 2001 Elsevier Science Ltd. All rights reserved.