Acetic acid (3aS,7S,7aR)-7-acetoxy-5-furan-2-yl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester | 146582-76-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (3aS,7S,7aR)-7-acetoxy-5-furan-2-yl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester
• 英文别名: [(3aR,4S,7aS)-7-acetyloxy-6-(furan-2-yl)-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-4-yl] acetate
• CAS: 146582-76-5
• 化学式: C₁₇H₂₂O₇
• 分子量: 338.357
• InChiKey: MAHRTBNTKUPUML-BOTDWXCTSA-N

物化性质

• 沸点：
  411.5±45.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  84.2
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aS,7S,7aR)-7-acetoxy-5-furan-2-yl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 在 ruthenium(IV) oxide sodium periodate 作用下， 以 四氯化碳 、 乙醚 、 水 、 乙腈 为溶剂， 生成 (3aS,7S,7aR)-4,7-Diacetoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of (+)- and (–)-methyl shikimate from benzene

  摘要：

  cis-Cyclohexa-3,5-diene-1,2-diol 2, the product of oxidation of benzene by mutants of Pseudomonas putida, was transformed into optically pure 4 in a sequence involving asymmetrization of meso-diol 3 in organic media with Pseudomonas cepacia lipase. Alcohol 4 was converted into the title compounds by processes utilizing alpha-iodination of the derived enones 8 and 9 followed by Pd0-catalysed coupling of the alpha-iodoenones with 2-tributylstannylfuran and RuO4-catalysed oxidation of the 2-furyl groups to carboxylic acids.

  DOI：

  10.1039/p19930000001
• 作为产物：
  描述：

  Acetic acid (3aS,7S,7aR)-7-acetoxy-5-furan-2-yl-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以97%的产率得到Acetic acid (3aS,7S,7aR)-7-acetoxy-5-furan-2-yl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester
  参考文献：
  名称：

  Synthesis of (+)- and (–)-methyl shikimate from benzene

  摘要：

  cis-Cyclohexa-3,5-diene-1,2-diol 2, the product of oxidation of benzene by mutants of Pseudomonas putida, was transformed into optically pure 4 in a sequence involving asymmetrization of meso-diol 3 in organic media with Pseudomonas cepacia lipase. Alcohol 4 was converted into the title compounds by processes utilizing alpha-iodination of the derived enones 8 and 9 followed by Pd0-catalysed coupling of the alpha-iodoenones with 2-tributylstannylfuran and RuO4-catalysed oxidation of the 2-furyl groups to carboxylic acids.

  DOI：

  10.1039/p19930000001