(3aRS,5RS,6SR,7aSR)-5,6-epoxy-perhydro-isobenzofuranon | 126632-00-6

• 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: (3aRS,5RS,6SR,7aSR)-5,6-epoxy-perhydro-isobenzofuranon
• 英文别名: (1aR,2aR,5aS,6aS)-2,2a,5,5a,6,6a-hexahydro-1aH-oxireno[2,3-f][2]benzofuran-3-one
• CAS: 126632-00-6；134732-12-0；145680-86-0；145680-92-8
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: QPZFHDWVZQLJJT-MVIOUDGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3aRS,5RS,6SR,7aSR)-5,6-epoxy-perhydro-isobenzofuranon 生成 (3aS,5R,6R,7aR)-5,6-dihydroxy-3a,4,5,6,7,7a-hexahydro-3H-2-benzofuran-1-one
  参考文献：
  名称：

  EDELSBACHER, A.;FLEISCHHACKER, W.;MOSTLER, U.;URBAN, E., SCI. PHARM., 56,(1988) N 1, 11

  摘要：

  DOI：
• 作为产物：
  描述：

  1-methyl hydrogen 1,2-cis-1,2-cyclohex-4-ene dicarboxylate 在 lithium hydroxide 、 锂硼氢 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (3aRS,5RS,6SR,7aSR)-5,6-epoxy-perhydro-isobenzofuranon
  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

• Synthese und Konfigurationszuordnung von potentiell antimikrobiellen 5,6-Dihydroxyisobenzofuranonen
  作者：Roswitha Stejskal、Ernst Urban、Horst V�llenkle

  DOI：10.1007/bf00809359

  日期：1991.3

  Oxidation of isobenzofuranone 1 yielded in a diastereoselective reaction epoxide 2. Acidolysis of 2 resulted in a mixture of trans-glycols 6 a (88%) and 7 a (4%), which were separated by crystallization. The relative configuration of 6 a and 7 a at the chiral centers 3 a, 5, 6, and 7 a was determined by H-1-NMR-spectroscopy and X-ray analysis of O-acetylated and 7 a-methylated derivatives.