(1S,2R,6S)-1-(3-methylbut-2-enyl)-7-oxa-bicyclo[4.1.0]heptan-2-yl benzoate | 1112053-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,6S)-1-(3-methylbut-2-enyl)-7-oxa-bicyclo[4.1.0]heptan-2-yl benzoate
• 英文别名: [(1S,2R,6S)-1-(3-methylbut-2-enyl)-7-oxabicyclo[4.1.0]heptan-2-yl] benzoate
• CAS: 1112053-64-1
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: SUSMMELXQDVQKG-SOLBZPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (1S,2R,6S)-1-(3-methylbut-2-enyl)-7-oxa-bicyclo[4.1.0]heptan-2-yl benzoate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以95%的产率得到(1aR,3aS,7R,7aS)-2,2-dimethyl-1a,3a,4,5,6,7-hexahydro-1H-cyclopropa[c][1]benzofuran-7-ol
  参考文献：
  名称：

  An Efficient Method for Construction of the Angularly Fused 6,3,5-Tricyclic Skeleton of Mycorrhizin A and Its Analogues

  摘要：

  The angularly fused 6,3,5-tricyclic system is readily generated via a cascade cyclization under acid promotion. The reaction proceeds at room temperature with high stereochemical fidelity from the electrophilic center of the epoxide to the cyclopropane product. This methodology provides a potentially useful approach for the synthesis of mycorrhizin A and its analogues.

  DOI：

  10.1021/ol8026895
• 作为产物：
  描述：

  (1R,2R,6S)-1-(3-methylbut-2-enyl)-7-oxabicyclo[4.1.0]heptan-2-ol 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到(1S,2R,6S)-1-(3-methylbut-2-enyl)-7-oxa-bicyclo[4.1.0]heptan-2-yl benzoate
  参考文献：
  名称：

  An Efficient Method for Construction of the Angularly Fused 6,3,5-Tricyclic Skeleton of Mycorrhizin A and Its Analogues

  摘要：

  The angularly fused 6,3,5-tricyclic system is readily generated via a cascade cyclization under acid promotion. The reaction proceeds at room temperature with high stereochemical fidelity from the electrophilic center of the epoxide to the cyclopropane product. This methodology provides a potentially useful approach for the synthesis of mycorrhizin A and its analogues.

  DOI：

  10.1021/ol8026895

文献信息

• An Efficient Method for Construction of the Angularly Fused 6,3,5-Tricyclic Skeleton of Mycorrhizin A and Its Analogues
  作者：Binxun Yu、Tuo Jiang、Weiguo Quan、Junpeng Li、Xinfu Pan、Xuegong She

  DOI：10.1021/ol8026895

  日期：2009.2.5

  The angularly fused 6,3,5-tricyclic system is readily generated via a cascade cyclization under acid promotion. The reaction proceeds at room temperature with high stereochemical fidelity from the electrophilic center of the epoxide to the cyclopropane product. This methodology provides a potentially useful approach for the synthesis of mycorrhizin A and its analogues.