1-(4-pyridyl)ethynyl-3-ethynylbicyclo[1.1.1]pentane | 457069-85-1

• 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: 1-(4-pyridyl)ethynyl-3-ethynylbicyclo[1.1.1]pentane
• 英文别名: 4-[2-(3-Ethynyl-1-bicyclo[1.1.1]pentanyl)ethynyl]pyridine
• CAS: 457069-85-1
• 化学式: C₁₄H₁₁N
• 分子量: 193.248
• InChiKey: HVUBGKXCWGKCIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3,5-三碘苯 、 1-(4-pyridyl)ethynyl-3-ethynylbicyclo[1.1.1]pentane 在 哌啶 、 四(三苯基膦)钯 作用下， 反应 18.0h， 以54%的产率得到1,3,5-tris((3-(4-pyridyl)ethynyl)bicyclo[1.1.1]pent-1-ylethynyl)benzene
  参考文献：
  名称：

  Synthesis and Structure of Trigonal and Tetragonal Connectors for a “Tinkertoy” Construction Set

  摘要：

  We describe a convergent synthesis of eight 1,3,5- and 1,2,4,5-substituted benzene derivatives with long rigid arms containing 4-pyridyl, 2,2'-bipyridyl, and 2,2'-bipyrimidyl termini, meant to be used as trigonal or tetragonal connectors for the construction of large molecular structures. The synthesis involved copper-free Pd-mediated coupling of terminal acetylenes to aryl halides. First, one of the termini of 1,3-diethynylbicyclo [1.1.1] pentane was coupled with a brominated aza heterocycle, and second, 3 equiv of the resulting extended arm were coupled with 1,3,5-triiodobenzene or 4 with 1,2,4,5-tetraiodobenzene. An improved large-scale synthesis for 1,3-diethynylbicyclo[1.1.1]pentane is described. The structures of two of the arms were determined by single-crystal X-ray analysis. Several long molecular rods with 4-pyridyl termini were obtained as byproducts, and a single-crystal X-ray structure is reported for the shortest of these.

  DOI：

  10.1021/jo020111b
• 作为产物：
  描述：

  1,3-Diethinylbicyclo<1.1.1>pentan 、 4-溴吡啶盐酸盐 在 哌啶 、 四(三苯基膦)钯 作用下， 反应 15.0h， 以73%的产率得到1-(4-pyridyl)ethynyl-3-ethynylbicyclo[1.1.1]pentane
  参考文献：
  名称：

  Synthesis and Structure of Trigonal and Tetragonal Connectors for a “Tinkertoy” Construction Set

  摘要：

  We describe a convergent synthesis of eight 1,3,5- and 1,2,4,5-substituted benzene derivatives with long rigid arms containing 4-pyridyl, 2,2'-bipyridyl, and 2,2'-bipyrimidyl termini, meant to be used as trigonal or tetragonal connectors for the construction of large molecular structures. The synthesis involved copper-free Pd-mediated coupling of terminal acetylenes to aryl halides. First, one of the termini of 1,3-diethynylbicyclo [1.1.1] pentane was coupled with a brominated aza heterocycle, and second, 3 equiv of the resulting extended arm were coupled with 1,3,5-triiodobenzene or 4 with 1,2,4,5-tetraiodobenzene. An improved large-scale synthesis for 1,3-diethynylbicyclo[1.1.1]pentane is described. The structures of two of the arms were determined by single-crystal X-ray analysis. Several long molecular rods with 4-pyridyl termini were obtained as byproducts, and a single-crystal X-ray structure is reported for the shortest of these.

  DOI：

  10.1021/jo020111b

文献信息

• Synthesis and Structure of Trigonal and Tetragonal Connectors for a “Tinkertoy” Construction Set
  作者：Peter F. H. Schwab、Bruce C. Noll、Josef Michl

  DOI：10.1021/jo020111b

  日期：2002.8.1

  We describe a convergent synthesis of eight 1,3,5- and 1,2,4,5-substituted benzene derivatives with long rigid arms containing 4-pyridyl, 2,2'-bipyridyl, and 2,2'-bipyrimidyl termini, meant to be used as trigonal or tetragonal connectors for the construction of large molecular structures. The synthesis involved copper-free Pd-mediated coupling of terminal acetylenes to aryl halides. First, one of the termini of 1,3-diethynylbicyclo [1.1.1] pentane was coupled with a brominated aza heterocycle, and second, 3 equiv of the resulting extended arm were coupled with 1,3,5-triiodobenzene or 4 with 1,2,4,5-tetraiodobenzene. An improved large-scale synthesis for 1,3-diethynylbicyclo[1.1.1]pentane is described. The structures of two of the arms were determined by single-crystal X-ray analysis. Several long molecular rods with 4-pyridyl termini were obtained as byproducts, and a single-crystal X-ray structure is reported for the shortest of these.