(3aR,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-5-(furan-2-yl)-2,2-dimethyl-7,7a-dihydro-3aH-1,3-benzodioxol-4-one | 146582-77-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-5-(furan-2-yl)-2,2-dimethyl-7,7a-dihydro-3aH-1,3-benzodioxol-4-one
• CAS: 146582-77-6
• 化学式: C₁₉H₂₈O₅Si
• 分子量: 364.514
• InChiKey: YZIUFHKJWIFERT-UAGQMJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-5-(furan-2-yl)-2,2-dimethyl-7,7a-dihydro-3aH-1,3-benzodioxol-4-one 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 24.25h， 生成 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
• 作为产物：
  描述：

  2-(三丁基锡烷基)呋喃 、 (3aR,7S,7aS)-7-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one 在 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三苯胂 作用下， 以 various solvent(s) 为溶剂， 以93%的产率得到(3aR,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-5-(furan-2-yl)-2,2-dimethyl-7,7a-dihydro-3aH-1,3-benzodioxol-4-one
  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

文献信息

• Synthesis of (+)- and (–)-methyl shikimate from benzene
  作者：Carl R. Johnson、Joseph P. Adams、Mark A. Collins

  DOI：10.1039/p19930000001

  日期：——

  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.