(3aR,4R,7R,7aS)-4,7-diacetyloxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-5-carboxylic acid | 1052649-85-0

• 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: (3aR,4R,7R,7aS)-4,7-diacetyloxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-5-carboxylic acid
• CAS: 1052649-85-0
• 化学式: C₁₄H₂₀O₈
• 分子量: 316.308
• InChiKey: XHJCWCMYUKPWRN-IPDPYQKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aR,4R,7R,7aS)-4,7-diacetyloxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-5-carboxylic acid 在 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 methyl shikimate
  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：

  [(3aS,4R,7R,7aR)-6-(furan-2-yl)-7-hydroxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-4-yl] acetate 在 ruthenium(IV) oxide 4-二甲氨基吡啶 、 sodium periodate 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (3aR,4R,7R,7aS)-4,7-diacetyloxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-5-carboxylic acid
  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