ethyl 4-(3-iodoprop-1-ynyl)-2-oxotetrahydro-2H-pyran-3-carboxylate. | 1042163-23-4

• 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: ethyl 4-(3-iodoprop-1-ynyl)-2-oxotetrahydro-2H-pyran-3-carboxylate.
• CAS: 1042163-23-4
• 化学式: C₁₁H₁₃IO₄
• 分子量: 336.126
• InChiKey: AMEUBCMJQBLVJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(3-iodoprop-1-ynyl)-2-oxotetrahydro-2H-pyran-3-carboxylate. 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以39%的产率得到ethyl 2-oxo-7-vinylidene-3-oxabicyclo[4.1.0]heptane-1-carboxylate
  参考文献：
  名称：

  An “Anti-Baldwin” 3-Exo-Dig Cyclization: Preparation of Vinylidene Cyclopropanes from Electron-Poor Alkenes

  摘要：

  Stabilized carbanions undergo an uncommon 3-exodig cyclization onto propargyl halides through an S(N)2' substitution. Propargyl iodides as electrophiles are necessary to achieve good yields (36-95%) for most substrates, although the usefulness of chlorides and bromides is documented. A variety of monocyclic and bicyclic; vinylidene cycloproparies can be prepared. These products are not available by standard carbene methodology.

  DOI：

  10.1021/ja803553a
• 作为产物：
  描述：

  ethyl 4-(3-chloroprop-1-ynyl)-2-oxotetrahydro-2H-pyran-3-carboxylate. 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 0.75h， 以49%的产率得到ethyl 4-(3-iodoprop-1-ynyl)-2-oxotetrahydro-2H-pyran-3-carboxylate.
  参考文献：
  名称：

  An “Anti-Baldwin” 3-Exo-Dig Cyclization: Preparation of Vinylidene Cyclopropanes from Electron-Poor Alkenes

  摘要：

  Stabilized carbanions undergo an uncommon 3-exodig cyclization onto propargyl halides through an S(N)2' substitution. Propargyl iodides as electrophiles are necessary to achieve good yields (36-95%) for most substrates, although the usefulness of chlorides and bromides is documented. A variety of monocyclic and bicyclic; vinylidene cycloproparies can be prepared. These products are not available by standard carbene methodology.

  DOI：

  10.1021/ja803553a