2-bromobenzyl-3-pyridine | 795309-03-4

• 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: 2-bromobenzyl-3-pyridine
• 英文别名: 3-[(2-Bromophenyl)methyl]pyridine
• CAS: 795309-03-4
• 化学式: C₁₂H₁₀BrN
• 分子量: 248.122
• InChiKey: CARYCNJCWXSDBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  2-bromobenzyl-3-pyridine 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 N-methyl-3-(2'-methoxybiphenyl-2-ylmethyl)pyridinium iodide
  参考文献：
  名称：

  Orientation and Alkylation Effects on Cation-π Interactions in Aqueous Solution

  摘要：

  We have investigated the orientation dependence of the cation-pi interaction between a phenyl ring and a pyridinium ring in the context of a flexible model system in water. Of the four possible positions of the pyridinium nitrogen, ipso, ortho, meta, and para, we found a variation in the interaction energy of about 0.75 kcal mol(-1), with the stacking of the ipso-pyridinium ring providing the strongest interaction. The observed stability is attributed to the maximization of the electrostatic interaction, minimization of rotamers, and possible differences in hydration phenomena arising from alkylation.

  DOI：

  10.1021/ja0498538
• 作为产物：
  描述：

  (2-bromophenyl)(pyridin-3-yl)methanol 在 吡啶 、 4-二甲氨基吡啶 、 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-bromobenzyl-3-pyridine
  参考文献：
  名称：

  Orientation and Alkylation Effects on Cation-π Interactions in Aqueous Solution

  摘要：

  We have investigated the orientation dependence of the cation-pi interaction between a phenyl ring and a pyridinium ring in the context of a flexible model system in water. Of the four possible positions of the pyridinium nitrogen, ipso, ortho, meta, and para, we found a variation in the interaction energy of about 0.75 kcal mol(-1), with the stacking of the ipso-pyridinium ring providing the strongest interaction. The observed stability is attributed to the maximization of the electrostatic interaction, minimization of rotamers, and possible differences in hydration phenomena arising from alkylation.

  DOI：

  10.1021/ja0498538

文献信息

• Orientation and Alkylation Effects on Cation-π Interactions in Aqueous Solution
  作者：Mark J. Rashkin、Robert M. Hughes、Nathaniel T. Calloway、Marcey L. Waters

  DOI：10.1021/ja0498538

  日期：2004.10.1

  We have investigated the orientation dependence of the cation-pi interaction between a phenyl ring and a pyridinium ring in the context of a flexible model system in water. Of the four possible positions of the pyridinium nitrogen, ipso, ortho, meta, and para, we found a variation in the interaction energy of about 0.75 kcal mol(-1), with the stacking of the ipso-pyridinium ring providing the strongest interaction. The observed stability is attributed to the maximization of the electrostatic interaction, minimization of rotamers, and possible differences in hydration phenomena arising from alkylation.