(3aR,5R,6S,7aS)-5,6-epoxy-perhydro-isobenzofuranone | 145680-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (3aR,5R,6S,7aS)-5,6-epoxy-perhydro-isobenzofuranone
• 英文别名: (1aS,2aS,5aR,6aR)-2,2a,5,5a,6,6a-hexahydro-1aH-oxireno[2,3-f][2]benzofuran-3-one
• CAS: 145680-86-0
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: QPZFHDWVZQLJJT-YTLHQDLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,7aS)-5,6-epoxy-perhydro-isobenzofuranone 在 DOWEX 50 WX₈ 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 以45%的产率得到(3aS,5S,6S,7aR)-5,6-dihydroxy-perhydro-isobenzofuranone
  参考文献：
  名称：

  Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones

  摘要：

  Optically pure available lactones 1 and 5 were diastereoselectively oxidised to cis-diols 2 and 6 by KMnO4 and to epoxides 3 and 7 by 3-chloroperoxybenzoic acid. Epoxide 3 was cleaved to trans-diol 4, whereas hydrolysis of 7 afforded tricyclic carboxylic acid 8. Optically pure dihydroxylactones 2, 4, and 6 are valuable models for structure determination of the antimicrobial garlic component garlicin.

  DOI：

  10.1007/bf00812323
• 作为产物：
  描述：

  8-oxabicyclo[4.3.0]non-3-en-9-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以89%的产率得到(3aR,5R,6S,7aS)-5,6-epoxy-perhydro-isobenzofuranone
  参考文献：
  名称：

  Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones

  摘要：

  Optically pure available lactones 1 and 5 were diastereoselectively oxidised to cis-diols 2 and 6 by KMnO4 and to epoxides 3 and 7 by 3-chloroperoxybenzoic acid. Epoxide 3 was cleaved to trans-diol 4, whereas hydrolysis of 7 afforded tricyclic carboxylic acid 8. Optically pure dihydroxylactones 2, 4, and 6 are valuable models for structure determination of the antimicrobial garlic component garlicin.

  DOI：

  10.1007/bf00812323

文献信息

• Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones
  作者：Anna Edelsbacher、Ernst Urban、Waltraud Weidenauer

  DOI：10.1007/bf00812323

  日期：——

  Optically pure available lactones 1 and 5 were diastereoselectively oxidised to cis-diols 2 and 6 by KMnO4 and to epoxides 3 and 7 by 3-chloroperoxybenzoic acid. Epoxide 3 was cleaved to trans-diol 4, whereas hydrolysis of 7 afforded tricyclic carboxylic acid 8. Optically pure dihydroxylactones 2, 4, and 6 are valuable models for structure determination of the antimicrobial garlic component garlicin.

表征谱图