7-(2-methoxybenzyl)-1,4-dimethyl-2,3,5,6-tetraoxa-bicyclo[2.2.1]heptane | 1142402-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 7-(2-methoxybenzyl)-1,4-dimethyl-2,3,5,6-tetraoxa-bicyclo[2.2.1]heptane
• 英文别名: 7-[(2-Methoxyphenyl)methyl]-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane
• CAS: 1142402-35-4
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: XZQYFQXLWQLDSR-UHFFFAOYSA-N

物化性质

• 熔点：
  46-48 °C
• 沸点：
  281.9±29.0 °C(predicted)
• 密度：
  1.253±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(2-methoxybenzyl)-1,4-dimethyl-2,3,5,6-tetraoxa-bicyclo[2.2.1]heptane 、 正丁醇 在 硫酸 、 双氧水 作用下， 以 水 为溶剂， 以72%的产率得到butyl (2-methoxyphenyl)acetate
  参考文献：
  名称：

  过氧化氢氧化取代的β-二酮：通过形成桥联的1,2,4,5-四恶烷合成酯

  摘要：

  在乙醇和强酸（硫酸，四氟硼酸或高氯酸）的混合物中，过氧化氢在79-120℃下用酸催化的烷基和苄基取代的β-二酮的氧化反应，生成相应的酯。形成桥接的1,2,4,5-四恶烷。 酯-过氧化氢-氧化-四恶烷-酮

  DOI：

  10.1055/s-0029-1219225
• 作为产物：
  描述：

  3-(2-methoxybenzyl)pentane-2,4-dione 在 硫酸 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 以54%的产率得到7-(2-methoxybenzyl)-1,4-dimethyl-2,3,5,6-tetraoxa-bicyclo[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.
• Oxidation of Substituted β-Diketones with Hydrogen Peroxide: Synthesis of Esters through the Formation of Bridged 1,2,4,5-Tetraoxanes
  作者：Alexander Terent’ev、Dmitry Borisov、Ivan Yaremenko、Yuri Ogibin、Gennady Nikishin

  DOI：10.1055/s-0029-1219225

  日期：2010.4

  Acid-catalyzed oxidation of alkyl- and benzyl-substituted β-diketones by hydrogen peroxide at 79-120 ˚C in a mixture of an alcohol and a strong acid (sulfuric acid, tetrafluoroboric acid, or perchloric acid) gave the corresponding esters through the formation of bridged 1,2,4,5-tetraoxanes. esters - hydrogen peroxide - oxidations - tetraoxanes - ketones

  在乙醇和强酸（硫酸，四氟硼酸或高氯酸）的混合物中，过氧化氢在79-120℃下用酸催化的烷基和苄基取代的β-二酮的氧化反应，生成相应的酯。形成桥接的1,2,4,5-四恶烷。 酯-过氧化氢-氧化-四恶烷-酮