1,4-dimethyl-7-(oxiran-2-ylmethyl)-2,3,5,6-tetraoxabicyclo[2.2.1]heptane | 1142402-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 1,4-dimethyl-7-(oxiran-2-ylmethyl)-2,3,5,6-tetraoxabicyclo[2.2.1]heptane
• CAS: 1142402-43-4
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: AIUVBFPJHAPCQE-UHFFFAOYSA-N

物化性质

• 沸点：
  187.6±29.0 °C(predicted)
• 密度：
  1.375±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-allyl-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane 在 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 96.0h， 以68%的产率得到1,4-dimethyl-7-(oxiran-2-ylmethyl)-2,3,5,6-tetraoxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Facile and Selective Procedure for the Synthesis of Bridged 1,2,4,5-Tetraoxanes; Strong Acids As Cosolvents and Catalysts for Addition of Hydrogen Peroxide to β-Diketones

  摘要：

  A facile, experimentally simple, and selective method was developed for the synthesis of bridged 1,2,4,5-tetraoxanes based on the reaction of hydrogen peroxide with beta-diketones catalyzed by strong acids (H2SO4, HClO4, HBF4, or BF3). The yields of the target products vary from 44% to 77%. 1,2,4,5-Tetraoxanes can easily be separated from other reaction products by column chromatography. A high concentration of a strong acid is a key factor determining the selectivity of formation and the yield of 1,2,4,5-tetraoxanes. Unlike many compounds containing the O-O bond. which undergo rearrangements in acidic media, the resulting cyclic peroxides are quite stable under these conditions.

  DOI：

  10.1021/jo900226b

文献信息

• Facile and Selective Procedure for the Synthesis of Bridged 1,2,4,5-Tetraoxanes; Strong Acids As Cosolvents and Catalysts for Addition of Hydrogen Peroxide to β-Diketones
  作者：Alexander O. Terent’ev、Dmitry A. Borisov、Vladimir V. Chernyshev、Gennady I. Nikishin

  DOI：10.1021/jo900226b

  日期：2009.5.1

  A facile, experimentally simple, and selective method was developed for the synthesis of bridged 1,2,4,5-tetraoxanes based on the reaction of hydrogen peroxide with beta-diketones catalyzed by strong acids (H2SO4, HClO4, HBF4, or BF3). The yields of the target products vary from 44% to 77%. 1,2,4,5-Tetraoxanes can easily be separated from other reaction products by column chromatography. A high concentration of a strong acid is a key factor determining the selectivity of formation and the yield of 1,2,4,5-tetraoxanes. Unlike many compounds containing the O-O bond. which undergo rearrangements in acidic media, the resulting cyclic peroxides are quite stable under these conditions.