[(3aS,4R,7aS)-6-iodo-2,2-dimethyl-7-oxo-4,7a-dihydro-3aH-1,3-benzodioxol-4-yl] acetate | 146582-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aS,4R,7aS)-6-iodo-2,2-dimethyl-7-oxo-4,7a-dihydro-3aH-1,3-benzodioxol-4-yl] acetate
• CAS: 146582-72-1
• 化学式: C₁₁H₁₃IO₅
• 分子量: 352.126
• InChiKey: MVDKGPOJMGVPPC-FKTZTGRPSA-N

物化性质

• 沸点：
  391.4±42.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3aS,4R,7aS)-6-iodo-2,2-dimethyl-7-oxo-4,7a-dihydro-3aH-1,3-benzodioxol-4-yl] acetate 在 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三苯胂 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.02h， 生成 [(3aS,4R,7R,7aR)-6-(furan-2-yl)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxol-4-yl] acetate
  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：

  (4R,5S,6R)-4-O-acetoxy-5,6-di-O-isopropylidenecyclohex-2-ene-1-one 在 吡啶 、 碘 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到[(3aS,4R,7aS)-6-iodo-2,2-dimethyl-7-oxo-4,7a-dihydro-3aH-1,3-benzodioxol-4-yl] acetate
  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