2-bromobenzyl-2-pyridine | 795309-02-3

• 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-2-pyridine
• 英文别名: 2-(2-bromobenzyl)pyridine；2-[(2-Bromophenyl)methyl]pyridine
• CAS: 795309-02-3
• 化学式: C₁₂H₁₀BrN
• 分子量: 248.122
• InChiKey: AXYQPBBMNIXYPE-UHFFFAOYSA-N

物化性质

• 沸点：
  320.4±22.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

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-2-pyridine 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.05h， 以68%的产率得到(2-bromophenyl)(2-pyridyl)methanol
  参考文献：
  名称：

  多芳香基取代的甲醇的绿色合成方法

  摘要：

  本发明涉及多芳香基取代的甲醇的绿色合成方法，具体地，以多芳香基取代的甲烷为原料，采用碱作为添加剂，在极性非质子性溶剂中，氧化剂的条件下实现多芳香基取代的甲醇的高效合成。本发明方法，绿色环保，避免了使用昂贵的金属催化剂，具有成本低、反应步骤少、时间短、收率高等优点。

  公开号：

  CN112661696A
• 作为产物：
  描述：

  1,2-二溴苯 在 氢碘酸 、 magnesium 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 14.0h， 生成 2-bromobenzyl-2-pyridine
  参考文献：
  名称：

  在室温下无配体的铱催化的苄基-2-吡啶的脱氢邻位C-H硼氢化反应

  摘要：

  已经开发了一种方便且无配体的铱催化的苄基-2-吡啶的脱氢邻位CHH硼氢化反应。在存在催化量的[IrOMe（COD）] 2的情况下，使用频哪醇硼烷作为硼化试剂，反应在室温下平稳进行。该反应与许多官能团相容，以中等至极好的收率和优异的选择性提供了大量的正硼酸化产物。

  DOI：

  10.1002/adsc.201801292

文献信息

• Palladium-Catalyzed Decarboxylative Couplings of 2-(2-Azaaryl)acetates with Aryl Halides and Triflates
  作者：Rui Shang、Zhi-Wei Yang、Yan Wang、Song-Lin Zhang、Lei Liu

  DOI：10.1021/ja107103b

  日期：2010.10.20

  Pd-catalyzed decarboxylative cross-couplings of 2-(2-azaaryl)acetates with aryl halides and triflates have been discovered. This reaction is potentially useful for the synthesis of some functionalized pyridines, quinolines, pyrazines, benzoxazoles, and benzothiazoles. Theoretical analysis shows that the nitrogen atom at the 2-position of the heteroaromatics directly coordinates to Pd(II) in the decarboxylation

  已发现 Pd 催化的 2-(2-氮杂芳基) 乙酸酯与芳基卤化物和三氟甲磺酸酯的脱羧交叉偶联。该反应可用于合成一些官能化的吡啶、喹啉、吡嗪、苯并恶唑和苯并噻唑。理论分析表明，杂芳烃 2 位的氮原子直接与脱羧过渡态的 Pd(II) 配位。
• Copper-Catalyzed α-Methylenation of Benzylpyridines Using Dimethylacetamide as One-Carbon Source
  作者：Masaki Itoh、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol500655k

  日期：2014.4.4

  The direct alpha-methylenation of benzylpyridines was achieved using N,N-dimethylacetamide (DMA) as a one-carbon source under copper catalysis. An intermediary species was detected at an early stage, and a possible mechanism was proposed. Additionally, alpha-oxygenation and dimerization of benzylpyridines could also be performed efficiently.
• Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation–Deuteration of Heterobenzylic Methylenes
  作者：Yonghai Liu、Yang Yu、Chengyu Sun、Yiwei Fu、Zhiguo Mang、Lei Shi、Hao Li

  DOI：10.1021/acs.orglett.0c03108

  日期：2020.10.16

  We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.
• 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.