6-(bromomethyl)-4,4-dimethyl-6-phenyltetrahydro-2H-pyran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-(bromomethyl)-4,4-dimethyl-6-phenyltetrahydro-2H-pyran-2-one
• 英文别名: 6-(bromomethyl)-4,4-dimethyl-6-phenyloxan-2-one；6-(Bromomethyl)-4,4-dimethyl-6-phenyloxan-2-one
• 化学式: C₁₄H₁₇BrO₂
• 分子量: 297.192
• InChiKey: AGLXOEUPAYLNLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  3,3-dimethyl-5-phenylhex-5-enoic acid 在 双氧水 、 vanadia 、 溴化铵 、 尿素 作用下， 以 水 、 丙酮 为溶剂， 以97%的产率得到6-(bromomethyl)-4,4-dimethyl-6-phenyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Bromolactonization of alkenoic acids mediated by V2O5 via bromide to bromenium in situ oxidation

  摘要：

  An efficient protocol for the bromolactonization of alkenoic acids is presented that obviates the use of molecular bromine or exogenous bromenium sources. Vanadium (V) oxide catalyzes the in situ oxidation of bromide salts to bromenium (Br+) in a process mediated by urea-hydrogen peroxide complex. Initial mechanistic investigations indicate that the presence of urea does not accelerate the halolactonization reaction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.071

文献信息

• Bromolactonization of alkenoic acids mediated by V2O5 via bromide to bromenium in situ oxidation
  作者：McKenzie L. Campbell、Samuel A. Rackley、Lauren N. Giambalvo、Daniel C. Whitehead

  DOI：10.1016/j.tetlet.2014.08.071

  日期：2014.10

  An efficient protocol for the bromolactonization of alkenoic acids is presented that obviates the use of molecular bromine or exogenous bromenium sources. Vanadium (V) oxide catalyzes the in situ oxidation of bromide salts to bromenium (Br+) in a process mediated by urea-hydrogen peroxide complex. Initial mechanistic investigations indicate that the presence of urea does not accelerate the halolactonization reaction. (C) 2014 Elsevier Ltd. All rights reserved.
• Vanadium (V) oxide mediated bromolactonization of alkenoic acids
  作者：McKenzie L. Campbell、Samuel A. Rackley、Lauren N. Giambalvo、Daniel C. Whitehead

  DOI：10.1016/j.tet.2015.04.029

  日期：2015.6

  A full account of our recently communicated method for the V2O5 mediated bromolactonization of alkenoic acids is presented. Here we describe the extensive evaluation of the metal oxide catalyst, terminal oxidant, halide source, solvent system, and reaction temperature that resulted in optimal conditions employing 0.05 equiv V2O5, 3 equiv urea-hydrogen peroxide complex (UHF), and 3 equiv of NH4Br in an acetone:H2O (6:1) solvent system at room temperature. Additionally, we have expanded the substrate scope of the reaction with the aim of evaluating the functional group tolerance of the transformation. Further, we present preliminary data of a related halogenation of beta-diketones with our optimal conditions. Finally, we probed the role of urea in the transformation. (C) 2015 Elsevier Ltd. All rights reserved.