(+/-)-(3aS,4S,5R,7aR)-1,3,3a,4,5,7a-hexahydro-2-benzofuran-4,5-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: (+/-)-(3aS,4S,5R,7aR)-1,3,3a,4,5,7a-hexahydro-2-benzofuran-4,5-diol
• 英文别名: (3aR,4R,5S,7aS)-1,3,3a,4,5,7a-hexahydro-2-benzofuran-4,5-diol
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: HAJMHDODSXNVGM-VGRMVHKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(3aS,4S,5R,7aR)-1,3,3a,4,5,7a-hexahydro-2-benzofuran-4,5-diol 、 乙酸酐 在 吡啶 作用下， 反应 25.0h， 以11.02 g的产率得到(+/-)-(3aS,4S,5R,7aR)-4-acetoxy-1,3,3a,4,5,7a-hexahydro-2-benzofuran-5-yl acetate
  参考文献：
  名称：

  Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors

  摘要：

  For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. The combination of these reactions resulted in the formation of various new inositol derivatives such as bishomo-chiro-inositol, bishomo-myo-inositol, and two isomeric bishomo-allo-inositols.

  DOI：

  10.1021/jo801344f
• 作为产物：
  描述：

  (3aRS,7aSR)-1,3,3a,7a-tetrahydroisobenzofuran 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 (+/-)-(3aS,4S,5R,7aR)-1,3,3a,4,5,7a-hexahydro-2-benzofuran-4,5-diol
  参考文献：
  名称：

  Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors

  摘要：

  For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. The combination of these reactions resulted in the formation of various new inositol derivatives such as bishomo-chiro-inositol, bishomo-myo-inositol, and two isomeric bishomo-allo-inositols.

  DOI：

  10.1021/jo801344f

文献信息

• Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors
  作者：Arif Baran、Metin Balci

  DOI：10.1021/jo801344f

  日期：2009.1.2

  For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. The combination of these reactions resulted in the formation of various new inositol derivatives such as bishomo-chiro-inositol, bishomo-myo-inositol, and two isomeric bishomo-allo-inositols.