3-[3'-(diethylboryl)phenyl]pyridine | 247214-57-9

• 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: 3-[3'-(diethylboryl)phenyl]pyridine
• 英文别名: Diethyl-(3-pyridin-3-ylphenyl)borane
• CAS: 247214-57-9
• 化学式: C₁₅H₁₈BN
• 分子量: 223.126
• InChiKey: ZYHNYPFGRSMFTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  溴苯 、 3-[3'-(diethylboryl)phenyl]pyridine 在 四(三苯基膦)钯 氢氧化钾 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以79.7%的产率得到3-([1,1′-biphenyl]-3-yl)pyridine
  参考文献：
  名称：

  Self-Assembly of 3-[4‘-(Diethylboryl)phenyl]pyridine and 3-[3‘-(Diethylboryl)phenyl]pyridine:  Synthesis, Structural Features, and Stability in Solution

  摘要：

  The self-assembly of 3-[4'-(diethylboryl)phenyl]pyridine (3) and 3-[3'-(diethylboryl)phenyl]pyridine (4) was investigated by H-1 and B-11 NMR spectroscopies and vapor pressure osmometry. It can be seen that in solution 3 affords an equilibrium mixture of oligomers including a cyclic trimer as a major component via intermolecular boron-nitrogen coordination bonds, which is supported by temperature-, concentration-, and solvent-dependent behaviors of 3. In contrast, 4 seems to afford a mixture of oligomers including a cyclic dimer in solution. Judging from the low coalescence temperature in variable-temperature NMR in toluene-d(8) and easy scrambling with the corresponding 3-[(diethylboryl)pheny]-5-methoxypyridines at ambient temperature, it is concluded that the intermolecular boron-nitrogen coordination bonds made by 3 or 4 are weaker than those formed by 3-(diethylboryl)pyridine (1) or 2-(diethylboryl)-5-methylpyridine (2). Poor thermal stability was supported by electrospray mass spectrometry and structural analyses utilizing a semi-empirical molecular orbital calculation AM1. It is noted that in the assembly of 4 there is a tendency to maintain high tetrahedral character at the boron atom in the complex at the expense of strain energy. Thus, these features of 3 and 4 in solution are in marked contrast to those of 1 and 2.

  DOI：

  10.1021/jo981632v
• 作为产物：
  描述：

  3-(三甲基锡烷基)-吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) copper(l) iodide 、 正丁基锂 、 四甲基乙二胺 、 三苯胂 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-[3'-(diethylboryl)phenyl]pyridine
  参考文献：
  名称：

  Self-Assembly of 3-[4‘-(Diethylboryl)phenyl]pyridine and 3-[3‘-(Diethylboryl)phenyl]pyridine:  Synthesis, Structural Features, and Stability in Solution

  摘要：

  The self-assembly of 3-[4'-(diethylboryl)phenyl]pyridine (3) and 3-[3'-(diethylboryl)phenyl]pyridine (4) was investigated by H-1 and B-11 NMR spectroscopies and vapor pressure osmometry. It can be seen that in solution 3 affords an equilibrium mixture of oligomers including a cyclic trimer as a major component via intermolecular boron-nitrogen coordination bonds, which is supported by temperature-, concentration-, and solvent-dependent behaviors of 3. In contrast, 4 seems to afford a mixture of oligomers including a cyclic dimer in solution. Judging from the low coalescence temperature in variable-temperature NMR in toluene-d(8) and easy scrambling with the corresponding 3-[(diethylboryl)pheny]-5-methoxypyridines at ambient temperature, it is concluded that the intermolecular boron-nitrogen coordination bonds made by 3 or 4 are weaker than those formed by 3-(diethylboryl)pyridine (1) or 2-(diethylboryl)-5-methylpyridine (2). Poor thermal stability was supported by electrospray mass spectrometry and structural analyses utilizing a semi-empirical molecular orbital calculation AM1. It is noted that in the assembly of 4 there is a tendency to maintain high tetrahedral character at the boron atom in the complex at the expense of strain energy. Thus, these features of 3 and 4 in solution are in marked contrast to those of 1 and 2.

  DOI：

  10.1021/jo981632v

文献信息

• Self-Assembly of 3-[4‘-(Diethylboryl)phenyl]pyridine and 3-[3‘-(Diethylboryl)phenyl]pyridine:  Synthesis, Structural Features, and Stability in Solution
  作者：Shigeharu Wakabayashi、Yoshikazu Sugihara、Katsuto Takakura、Shigeru Murata、Hideo Tomioka、Shiho Ohnishi、Kazuyuki Tatsumi

  DOI：10.1021/jo981632v

  日期：1999.9.1

  The self-assembly of 3-[4'-(diethylboryl)phenyl]pyridine (3) and 3-[3'-(diethylboryl)phenyl]pyridine (4) was investigated by H-1 and B-11 NMR spectroscopies and vapor pressure osmometry. It can be seen that in solution 3 affords an equilibrium mixture of oligomers including a cyclic trimer as a major component via intermolecular boron-nitrogen coordination bonds, which is supported by temperature-, concentration-, and solvent-dependent behaviors of 3. In contrast, 4 seems to afford a mixture of oligomers including a cyclic dimer in solution. Judging from the low coalescence temperature in variable-temperature NMR in toluene-d(8) and easy scrambling with the corresponding 3-[(diethylboryl)pheny]-5-methoxypyridines at ambient temperature, it is concluded that the intermolecular boron-nitrogen coordination bonds made by 3 or 4 are weaker than those formed by 3-(diethylboryl)pyridine (1) or 2-(diethylboryl)-5-methylpyridine (2). Poor thermal stability was supported by electrospray mass spectrometry and structural analyses utilizing a semi-empirical molecular orbital calculation AM1. It is noted that in the assembly of 4 there is a tendency to maintain high tetrahedral character at the boron atom in the complex at the expense of strain energy. Thus, these features of 3 and 4 in solution are in marked contrast to those of 1 and 2.