tetrahydro-3-(3-methylbut-2-enyl)pyran-2-one | 412026-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tetrahydro-3-(3-methylbut-2-enyl)pyran-2-one
• 英文别名: 3-(3-Methyl-but-2-enyl)-tetrahydro-pyran-2-one；3-(3-methylbut-2-enyl)oxan-2-one
• CAS: 412026-41-6
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: YCHMLWDBOCXEJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetrahydro-3-(3-methylbut-2-enyl)pyran-2-one 、 苯基溴化硒 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以68%的产率得到3-(3-methylbut-2-enyl)-3-(phenylselanyl)-tetrahydropyran-2-one
  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：

  delta-戊内酯 、 1-溴-3-甲基-2-丁烯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以91%的产率得到tetrahydro-3-(3-methylbut-2-enyl)pyran-2-one
  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.