(1aR,3aS,6aR,6bS)-6a-hydroxy-1a,3,3a,5,6,6b-hexahydrooxireno[2,3-e][1]benzofuran-2-one | 1159796-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1aR,3aS,6aR,6bS)-6a-hydroxy-1a,3,3a,5,6,6b-hexahydrooxireno[2,3-e][1]benzofuran-2-one
• CAS: 1159796-01-6
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: SOOZYIGRINXLFT-DKXJUACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  12
• 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：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1aR,3aS,6aR,6bS)-6a-hydroxy-1a,3,3a,5,6,6b-hexahydrooxireno[2,3-e][1]benzofuran-2-one 在 aluminum amalgam 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.67h， 以6.0 mg的产率得到(-)-cleroindicin D
  参考文献：
  名称：

  Enantioselective Total Synthesis of All of the Known Chiral Cleroindicins (C−F): Clarification Among Optical Rotations and Assignments

  摘要：

  Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.

  DOI：

  10.1021/jo900401k
• 作为产物：
  描述：

  rengyolone 在 Ph₃COOK 作用下， 以 四氢呋喃 为溶剂， 生成 (1aR,3aS,6aR,6bS)-6a-hydroxy-1a,3,3a,5,6,6b-hexahydrooxireno[2,3-e][1]benzofuran-2-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of All of the Known Chiral Cleroindicins (C−F): Clarification Among Optical Rotations and Assignments

  摘要：

  Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.

  DOI：

  10.1021/jo900401k