5-bromo-2-tert-butyl-2-methyl-1,3-dioxane-4,6-dione | 916057-04-0

• 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: 5-bromo-2-tert-butyl-2-methyl-1,3-dioxane-4,6-dione
• CAS: 916057-04-0
• 化学式: C₉H₁₃BrO₄
• 分子量: 265.104
• InChiKey: ICVUTODLQBSMNI-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  380.7±42.0 °C(Predicted)
• 密度：
  1.468±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-bromo-2-tert-butyl-2-methyl-1,3-dioxane-4,6-dione 以 四氢呋喃 、 甲醇 为溶剂， 反应 27.0h， 生成 2-tert-butyl-2,5-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Chemistry of diazocarbonyl compounds: XXV. Comparative photochemistry of diazo compounds and sulfur ylides of the 1,3-dioxane-4,6-dione series

  摘要：

  Photochemical decomposition of 2,2-dialkyl-5-diazo-1,3-dioxane-4,6-diones in the presence of pyridine, methanol.. or dimethyl sulfide as carbene traps involves mainly the Wolff rearrangement which is likely to follow a concerted pattern, while the yield of the "carbene" products does not exceed 27-28%. No carbene intermediates are formed in the photolysis of the corresponding dioxo sulfonium ylides under analogous conditions, and the main photochemical process is 1,2-methyl shift (Stevens rearrangement), followed by photochemical transformations of the primary products according to the Norrish type 11 pattern.

  DOI：

  10.1134/s1070428006060029
• 作为产物：
  描述：

  2-methyl-2-tert-butyl-1,3-dioxane-4,6-dione 在 sodium hydroxide 、 溴 作用下， 以 水 为溶剂， 反应 0.67h， 以76%的产率得到5-bromo-2-tert-butyl-2-methyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Chemistry of diazocarbonyl compounds: XXV. Comparative photochemistry of diazo compounds and sulfur ylides of the 1,3-dioxane-4,6-dione series

  摘要：

  Photochemical decomposition of 2,2-dialkyl-5-diazo-1,3-dioxane-4,6-diones in the presence of pyridine, methanol.. or dimethyl sulfide as carbene traps involves mainly the Wolff rearrangement which is likely to follow a concerted pattern, while the yield of the "carbene" products does not exceed 27-28%. No carbene intermediates are formed in the photolysis of the corresponding dioxo sulfonium ylides under analogous conditions, and the main photochemical process is 1,2-methyl shift (Stevens rearrangement), followed by photochemical transformations of the primary products according to the Norrish type 11 pattern.

  DOI：

  10.1134/s1070428006060029