4-[(Z)-3,3-diethoxyprop-1-enyl]-2-[4-[(Z)-3,3-diethoxyprop-1-enyl]pyridin-2-yl]pyridine | 189000-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-[(Z)-3,3-diethoxyprop-1-enyl]-2-[4-[(Z)-3,3-diethoxyprop-1-enyl]pyridin-2-yl]pyridine
• CAS: 189000-99-5
• 化学式: C₂₄H₃₂N₂O₄
• 分子量: 412.529
• InChiKey: YLGYZIBJVWJVDJ-HWAYABPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(Z)-3,3-diethoxyprop-1-enyl]-2-[4-[(Z)-3,3-diethoxyprop-1-enyl]pyridin-2-yl]pyridine 在 草酸 作用下， 生成 (E)-3-[4'-((E)-3-Oxo-propenyl)-[2,2']bipyridinyl-4-yl]-propenal
  参考文献：
  名称：

  Synthesis of Cyclo-2,2‘:4‘,4‘‘:2‘‘,2‘‘‘:4‘‘‘,4‘‘‘‘:2‘‘‘‘,2‘‘‘‘‘:4‘‘‘‘‘,4-sexipyridine

  摘要：

  Preparation of the title compound (2) by use of Stille couplings and a Krohnke pyridine synthesis is described. By application of the Stille coupling reaction, preparation and functionalization of quater- and quinquepyridines 26, 27, and 28 were achieved. Elaboration of quinquepyridine 27 to the pyridinium salt 30 bearing a protected enal allowed for the synthesis of 2 by a one-pot deprotection/Krohnke reaction in nine steps from 4,4'-bipyridine. Use of the Krohnke pyridine synthesis has been applied to prepare sexipyridine dibromide 19, but attempts to induce a macrocyclization via metal-mediated (Pd/Ni/Cu) aryl-aryl coupling procedures proved unsuccessful. Acetylene-bridged sexipyridines 3a and 3b incorporating 2,2'-bipyridine units proved to be inaccessible via sp-sp(2) or sp-sp coupling protocols.

  DOI：

  10.1021/jo962236k
• 作为产物：
  描述：

  4,4'-二溴-2,2'-联吡啶 在 Lindlar's catalyst copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 氢气 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 4-[(Z)-3,3-diethoxyprop-1-enyl]-2-[4-[(Z)-3,3-diethoxyprop-1-enyl]pyridin-2-yl]pyridine
  参考文献：
  名称：

  Synthesis of Cyclo-2,2‘:4‘,4‘‘:2‘‘,2‘‘‘:4‘‘‘,4‘‘‘‘:2‘‘‘‘,2‘‘‘‘‘:4‘‘‘‘‘,4-sexipyridine

  摘要：

  Preparation of the title compound (2) by use of Stille couplings and a Krohnke pyridine synthesis is described. By application of the Stille coupling reaction, preparation and functionalization of quater- and quinquepyridines 26, 27, and 28 were achieved. Elaboration of quinquepyridine 27 to the pyridinium salt 30 bearing a protected enal allowed for the synthesis of 2 by a one-pot deprotection/Krohnke reaction in nine steps from 4,4'-bipyridine. Use of the Krohnke pyridine synthesis has been applied to prepare sexipyridine dibromide 19, but attempts to induce a macrocyclization via metal-mediated (Pd/Ni/Cu) aryl-aryl coupling procedures proved unsuccessful. Acetylene-bridged sexipyridines 3a and 3b incorporating 2,2'-bipyridine units proved to be inaccessible via sp-sp(2) or sp-sp coupling protocols.

  DOI：

  10.1021/jo962236k

文献信息

• Synthesis of Cyclo-2,2‘:4‘,4‘‘:2‘‘,2‘‘‘:4‘‘‘,4‘‘‘‘:2‘‘‘‘,2‘‘‘‘‘:4‘‘‘‘‘,4-sexipyridine
  作者：T. Ross Kelly、Yean-Jang Lee、Richard J. Mears

  DOI：10.1021/jo962236k

  日期：1997.5.1

  Preparation of the title compound (2) by use of Stille couplings and a Krohnke pyridine synthesis is described. By application of the Stille coupling reaction, preparation and functionalization of quater- and quinquepyridines 26, 27, and 28 were achieved. Elaboration of quinquepyridine 27 to the pyridinium salt 30 bearing a protected enal allowed for the synthesis of 2 by a one-pot deprotection/Krohnke reaction in nine steps from 4,4'-bipyridine. Use of the Krohnke pyridine synthesis has been applied to prepare sexipyridine dibromide 19, but attempts to induce a macrocyclization via metal-mediated (Pd/Ni/Cu) aryl-aryl coupling procedures proved unsuccessful. Acetylene-bridged sexipyridines 3a and 3b incorporating 2,2'-bipyridine units proved to be inaccessible via sp-sp(2) or sp-sp coupling protocols.