3-<(Z)-4-(Benzyloxy)-2-butenyl>tetrahydropyran-2-one

• 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: 3-<(Z)-4-(Benzyloxy)-2-butenyl>tetrahydropyran-2-one
• 英文别名: 3-[(Z)-4-phenylmethoxybut-2-enyl]oxan-2-one
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: ZQBLPKYHZTUSNL-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<(Z)-4-(Benzyloxy)-2-butenyl>tetrahydropyran-2-one 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-<(Z)-4-(Benzyloxy)-2-butenyl>-2-hydroxytetrahydropyran
  参考文献：
  名称：

  Catalytic Iron-Mediated Enediene Carbocyclizations: Investigations into the Stereoselective Formation of Bicyclic Ring Systems

  摘要：

  Trienes in which the requisite 1,3-diene and allylic ether moieties are appended to a pre-existing ring system afford bicyclic ring systems-upon iron-catalyzed cyclization. The efficiency and stereoselectivity of the cyclization are dramatically influenced by the nature of the ring system to which the diene and alkene subunits are appended. Certain bicyclic ring systems are formed in good yield; most notably, substrates bearing a basic nitrogen are well-tolerated and certain indolizidine and quinolizidine ring systems are accessible using this methodology. The efficiency and stereoselectivity of the cyclization is also markedly dependent on the ligand used to modify the iron catalyst, and in this regard, a bisoxazoline-modified iron catalyst system is generally superior to what was the standard bipyridine-modified catalyst. In the course of these studies a difference spin polarization transfer (DSPT) experiment proved very useful for the stereochemical analysis of compounds that exhibit very crowded high field NMR spectra.

  DOI：

  10.1021/jo00116a039
• 作为产物：
  描述：

  delta-戊内酯 、 (Z)-(((4-bromobut-2-en-1-yl)oxy)methyl)benzene 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 以72%的产率得到3-<(Z)-4-(Benzyloxy)-2-butenyl>tetrahydropyran-2-one
  参考文献：
  名称：

  Catalytic Iron-Mediated Enediene Carbocyclizations: Investigations into the Stereoselective Formation of Bicyclic Ring Systems

  摘要：

  Trienes in which the requisite 1,3-diene and allylic ether moieties are appended to a pre-existing ring system afford bicyclic ring systems-upon iron-catalyzed cyclization. The efficiency and stereoselectivity of the cyclization are dramatically influenced by the nature of the ring system to which the diene and alkene subunits are appended. Certain bicyclic ring systems are formed in good yield; most notably, substrates bearing a basic nitrogen are well-tolerated and certain indolizidine and quinolizidine ring systems are accessible using this methodology. The efficiency and stereoselectivity of the cyclization is also markedly dependent on the ligand used to modify the iron catalyst, and in this regard, a bisoxazoline-modified iron catalyst system is generally superior to what was the standard bipyridine-modified catalyst. In the course of these studies a difference spin polarization transfer (DSPT) experiment proved very useful for the stereochemical analysis of compounds that exhibit very crowded high field NMR spectra.

  DOI：

  10.1021/jo00116a039

文献信息

• Catalytic Iron-Mediated Enediene Carbocyclizations: Investigations into the Stereoselective Formation of Bicyclic Ring Systems
  作者：James M. Takacs、John J. Weidner、Peter W. Newsome、Beckie E. Takacs、Ramakrishnan Chidambaram、Richard Shoemaker

  DOI：10.1021/jo00116a039

  日期：1995.6

  Trienes in which the requisite 1,3-diene and allylic ether moieties are appended to a pre-existing ring system afford bicyclic ring systems-upon iron-catalyzed cyclization. The efficiency and stereoselectivity of the cyclization are dramatically influenced by the nature of the ring system to which the diene and alkene subunits are appended. Certain bicyclic ring systems are formed in good yield; most notably, substrates bearing a basic nitrogen are well-tolerated and certain indolizidine and quinolizidine ring systems are accessible using this methodology. The efficiency and stereoselectivity of the cyclization is also markedly dependent on the ligand used to modify the iron catalyst, and in this regard, a bisoxazoline-modified iron catalyst system is generally superior to what was the standard bipyridine-modified catalyst. In the course of these studies a difference spin polarization transfer (DSPT) experiment proved very useful for the stereochemical analysis of compounds that exhibit very crowded high field NMR spectra.