2-溴-3-(二溴甲基)-吡啶 | 865449-15-6

• 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
• 中文名称: 2-溴-3-(二溴甲基)-吡啶
• 英文名称: 2-bromo-3-(dibromomethyl)-pyridine
• 英文别名: 2-bromo-3-(dibromomethyl)pyridine；2-bromo-3-dibromomethyl-pyridine；2-Bromo-3-dibromomethyl-pyridine
• CAS: 865449-15-6
• 化学式: C₆H₄Br₃N
• 分子量: 329.816
• InChiKey: AMBNNMHUQYTFNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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-溴-3-(二溴甲基)-吡啶 在 水 、 calcium carbonate 作用下， 反应 7.0h， 以60%的产率得到2-溴-3-吡啶甲醛
  参考文献：
  名称：

  通过含有α-氨基酸残基的N-酰基胺离子的分子内级联环化非对映选择性合成旋转限制性手性苯基吡啶

  摘要：

  摘要 通过级联环化非对映选择性地合成了一系列具有稠合手性桥的手性苯基吡啶，其中涉及包括对映纯α-氨基酸残基的N-酰基胺离子。在文献方法的基础上，通过使用核 Overhauser 效应差异和圆二色性 (CD) 测量，明确确定了合成苯基吡啶的绝对构型。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要

  DOI：

  10.1080/00397911.2013.771403
• 作为产物：
  描述：

  2-氨基-3-甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 氢溴酸 、 溴 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 水 为溶剂， 反应 7.33h， 生成 2-溴-3-(二溴甲基)-吡啶
  参考文献：
  名称：

  The expedient access to bromo-pyridine carbaldehyde scaffolds using gem-dibromomethyl intermediates

  摘要：

  A simple, efficient, and general two-step synthesis to bromo-pyridine carbaldehyde scaffolds is described. This direct route involves sequential reactions employing the dibromination of bromo-picolines followed by hydrolysis using an aqueous solution of calcium carbonate. Bromo-pyridine carbaldehyde scaffolds 1-7 were obtained in good overall yield. Bromo-dibromomethyl-pyridine intermediates have been isolated and characterized. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.016

文献信息

• Diastereoselective Synthesis of Rotationally Restricted Chiral Phenylpyridines via Intramolecular Cascade Cyclization of <i>N</i>-Acyliminium Ions Containing <font>α</font>-Amino Acid Residues
  作者：Jin-Ling Li、Hong-Wu Zhao、Xiao Qin、Jin Cui、Shi Su、Hai-Long Li、Yuan-Yuan Yue、Xiu-Qing Song

  DOI：10.1080/00397911.2013.771403

  日期：2013.12.2

  Abstract A series of chiral phenylpyridines possessing a fused chiral bridge were synthesized diastereoselectively via cascade cyclizations, where N-acyliminium ions including an enantiopure α-amino acid residue were involved. The absolute configuration of the synthesized phenylpyridines was identified unambiguously by using nuclear Overhauser effect difference and circular dichroism (CD) measurements

  摘要 通过级联环化非对映选择性地合成了一系列具有稠合手性桥的手性苯基吡啶，其中涉及包括对映纯α-氨基酸残基的N-酰基胺离子。在文献方法的基础上，通过使用核 Overhauser 效应差异和圆二色性 (CD) 测量，明确确定了合成苯基吡啶的绝对构型。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• Synthesis and σ receptor affinity of regioisomeric spirocyclic furopyridines
  作者：Kengo Miyata、Dirk Schepmann、Bernhard Wünsch

  DOI：10.1016/j.ejmech.2014.06.073

  日期：2014.8

  In order to investigate systematically the effect of the position of the pyridine N-atom on the σ1 receptor affinity four regioisomeric furopyridines 2a-d were synthesized and pharmacologically evaluated. The key steps of the synthesis comprise bromine/lithium exchange at regioisomeric bromopyridinecarbaldehyde acetals 7a-d, subsequent addition to 1-benzylpiperidin-4-one and cyclization. The regioisomeric acetals 7a-d were obtained either by o-metalation of bromopyridines 5b and 5c or by oxidation of bromopicolines 3a and 3d. In radioligand binding studies the regioisomeric furopyridines 2a-d showed 7- to 12-fold lower σ1 affinity than the benzofuran analog 1. The reduced σ1 affinity of the furopyridines 2a-d is explained with the reduced electron density of the pyridine ring. Since the four regioisomeric furopyridines show almost the same σ1 affinity (Ki = 4.9-10 nM), a directed interaction of the pyridine N-atom with the receptor protein can be excluded.
• The expedient access to bromo-pyridine carbaldehyde scaffolds using gem-dibromomethyl intermediates
  作者：Ashis Baran Mandal、John Kallikat Augustine、Anna Quattropani、Agnes Bombrun

  DOI：10.1016/j.tetlet.2005.07.016

  日期：2005.9

  A simple, efficient, and general two-step synthesis to bromo-pyridine carbaldehyde scaffolds is described. This direct route involves sequential reactions employing the dibromination of bromo-picolines followed by hydrolysis using an aqueous solution of calcium carbonate. Bromo-pyridine carbaldehyde scaffolds 1-7 were obtained in good overall yield. Bromo-dibromomethyl-pyridine intermediates have been isolated and characterized. (c) 2005 Elsevier Ltd. All rights reserved.