5-bromo-5'-n-butyl-2,2'-bipyridine | 400859-04-3

• 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: 5-bromo-5'-n-butyl-2,2'-bipyridine
• 英文别名: 5-n-butyl-5'-bromo-2,2'-bipyridine；2-(5-Bromopyridin-2-yl)-5-butylpyridine
• CAS: 400859-04-3
• 化学式: C₁₄H₁₅BrN₂
• 分子量: 291.19
• InChiKey: CSAXLSXZEXDTNY-UHFFFAOYSA-N

物化性质

• 沸点：
  375.4±42.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-5'-n-butyl-2,2'-bipyridine 在 哌啶 、 四(三苯基膦)钯 、 三乙胺 作用下， 反应 27.0h， 生成 1,3,5-tris((3-(5'-n-butyl-2,2'-bipyridin-5-yl)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：

  2,5-二溴吡啶 、 5-n-butyl-2-trimethylstannylpyridine 在 四(三苯基膦)钯 作用下， 以 xylene 为溶剂， 反应 16.0h， 以79%的产率得到5-bromo-5'-n-butyl-2,2'-bipyridine
  参考文献：
  名称：

  制备5-溴和5,5'-二溴的2,2'-联吡啶和2,2'-联嘧啶。

  摘要：

  已经开发了可用于制备金属络合物分子棒的5-溴和5,5'-二溴的2,2'-联吡啶和2,2'-联嘧啶的有效合成方法。通过以下方法获得了5-溴-2,2'-联吡啶，5-溴-5'-正丁基-2,2'-联吡啶和5-溴-5'-正己基-2,2'-联吡啶2，5-二溴吡啶与2-三甲基苯乙烯基吡啶或必要的5-烷基-2-三甲基苯乙烯基吡啶的斯蒂勒偶联，是通过3-烷基吡啶.BF（3）络合物的区域选择性锌化而获得的，该络合物在较少受两个反应位置影响的情况下与二锂-叔丁基-（2,2,6,6-四甲基哌啶子基）锌酸酯。通过5，5′-二溴-2，2′-联吡啶通过2，5-二溴吡啶与六正丁基二锡烷的还原对称偶联而获得。这些偶联反应的产率为70-90％。

  DOI：

  10.1021/jo010707j

文献信息

• Preparation of 5-Brominated and 5,5‘-Dibrominated 2,2‘-Bipyridines and 2,2‘-Bipyrimidines
  作者：Peter F. H. Schwab、Frank Fleischer、Josef Michl

  DOI：10.1021/jo010707j

  日期：2002.1.1

  two reactive positions with lithium di-tert-butyl-(2,2,6,6-tetramethylpiperidino)zincate. 5,5'-Dibromo-2,2'-bipyridine was obtained by the reductive symmetric coupling of 2,5-dibromopyridine with hexa-n-butyldistannane. The yields of these coupling reactions ranged from 70 to 90%. 5-Bromo- and 5,5'-dibromo-2,2'-bipyrimidines were obtained in yields of 30 and 15%, respectively, by bromination of 2,2'-bipyrimidine

  已经开发了可用于制备金属络合物分子棒的5-溴和5,5'-二溴的2,2'-联吡啶和2,2'-联嘧啶的有效合成方法。通过以下方法获得了5-溴-2,2'-联吡啶，5-溴-5'-正丁基-2,2'-联吡啶和5-溴-5'-正己基-2,2'-联吡啶2，5-二溴吡啶与2-三甲基苯乙烯基吡啶或必要的5-烷基-2-三甲基苯乙烯基吡啶的斯蒂勒偶联，是通过3-烷基吡啶.BF（3）络合物的区域选择性锌化而获得的，该络合物在较少受两个反应位置影响的情况下与二锂-叔丁基-（2,2,6,6-四甲基哌啶子基）锌酸酯。通过5，5′-二溴-2，2′-联吡啶通过2，5-二溴吡啶与六正丁基二锡烷的还原对称偶联而获得。这些偶联反应的产率为70-90％。
• 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.