1-<(Z)-4-(Benzyloxy)-2-butenyl>-2-((E)-2,4-pentadienyl)piperidine | 168783-49-1

• 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: 1-<(Z)-4-(Benzyloxy)-2-butenyl>-2-((E)-2,4-pentadienyl)piperidine
• 英文别名: 2-[(2E)-penta-2,4-dienyl]-1-[(Z)-4-phenylmethoxybut-2-enyl]piperidine
• CAS: 168783-49-1
• 化学式: C₂₁H₂₉NO
• 分子量: 311.467
• InChiKey: GJGUZDGGOPENLM-DWQQYCHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<(Z)-4-(Benzyloxy)-2-butenyl>-2-((E)-2,4-pentadienyl)piperidine 在 iron(III)-acetylacetonate 、 三乙基铝 、 (4R,4’R)-2,2’-(propane-2,2-diyl)bis(4-benzyl-4,5-dihydrooxazole) 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以70%的产率得到(2S,3R,9aR)-3-((E)-2-Benzyloxy-vinyl)-2-((Z)-propenyl)-octahydro-quinolizine
  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：

  1-((Z)-4-Benzyloxy-but-2-enyl)-6-methoxy-piperidin-2-one 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 1-<(Z)-4-(Benzyloxy)-2-butenyl>-2-((E)-2,4-pentadienyl)piperidine
  参考文献：
  名称：

  三烯的催化铁介导的烯碳环化：对某些双环内酰胺和胺的立体选择性形成的研究。

  摘要：

  使用铁催化的碳环化以立体选择性的方式构建某些双环系统（即，吲哚嗪和喹唑烷环系统）。值得注意的是，还原铁催化剂可耐受含有碱性氮的三烯底物，并且底物的性质（胺对酰胺）和配体的性质（在铁催化剂体系中使用的2，2′-联吡啶对双恶唑啉。

  DOI：

  10.1016/s0040-4039(00)73714-2

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.
• Catalytic iron-mediated ene carbocyclizations of trienes: Investigations into the stereoselective formation of some bicyclic lactams and amines.
  作者：James M. Takacs、John J. Weidner、Beckie E. Takacs

  DOI：10.1016/s0040-4039(00)73714-2

  日期：1993.9

  Certain bicyclic ring systems (i.e., indolizidine and quinolizidine ring systems) are constructed in a stereoselective fashion using an iron-catalyzed carbocyclization. It is noteworthy that the reduced iron catalyst tolerates triene substrates containing a basic nitrogen and that the chemical efficiency and the degree of 1,3-stereoinduction are dramatically influenced by the nature of the substrate

  使用铁催化的碳环化以立体选择性的方式构建某些双环系统（即，吲哚嗪和喹唑烷环系统）。值得注意的是，还原铁催化剂可耐受含有碱性氮的三烯底物，并且底物的性质（胺对酰胺）和配体的性质（在铁催化剂体系中使用的2，2′-联吡啶对双恶唑啉。