3-bromopyridinium ethylformate chloride | 92915-13-4

• 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-bromopyridinium ethylformate chloride
• 英文别名: ethyl 3-bromopyridin-1-ium-1-carboxylate;chloride
• CAS: 92915-13-4
• 化学式: C₈H₉BrNO₂*Cl
• 分子量: 266.522
• InChiKey: PILYBTLIKHOROI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.25
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.18
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-bromopyridinium ethylformate chloride 在 Raney-Co 正丁基锂 、 氢气 、 lithium chloride 、 锌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， -78.0~50.0 ℃ 、620.54 kPa 条件下， 反应 90.5h， 生成 [4aS-(4aα,9bβ)]-(+)-2H-1,4a-ethano-3,4,5,9b-tetrahydro1H-cyclopenta[2,1-b:3,4-c']dipyridine dihydrochloride
  参考文献：
  名称：

  Conformationally Constrained Nicotines:  Polycyclic, Bridged, and Spiro-Annulated Analogues as Novel Ligands for the Nicotinic Acetylcholine Receptor

  摘要：

  A set of novel nicotine-related, conformationally constrained compounds, including tetracyclic, bridged (4), and tricyclic, spiro-annulated (5) structures, were synthesized in a straightforward manner and optically resolved in a convenient fashion with (+)- and (-)-O,O'-di-p-toluoyltartaric acids. Absolute configurations were determined by X-ray crystallography. These compounds were evaluated for their ability to displace [H-3]cytisine in a rat forebrain preparation and compared to (-)-nicotine. Three substances emerged with high affinity in the low nanomolar range. Moreover, one of these compounds ((+)-5b) showed not only high binding affinity (K-i = 4.79 nM) but also significant enantioselectivity over its antipode (K-i = 148 nM), supporting the hypothesis that conformational restraint can lead to high-affinity ligands, which are stereochemically discriminated by the nicotinic acetylcholine receptor and may feature optimum locations of the active sites of the pharmacophore.

  DOI：

  10.1021/jm020916b
• 作为产物：
  描述：

  3-溴吡啶 、 氯甲酸乙酯 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3-bromopyridinium ethylformate chloride
  参考文献：
  名称：

  Shiao, Min-Jen; Chia, Win-Long; Shing, Tai-Li, Journal of Chemical Research, Miniprint, 1992, p. 2101 - 2121

  摘要：

  DOI：

文献信息

• A facile synthesis of functionalized 4-benzylpyridines by using mixed copper, zinc benzylic organometallics
  作者：Win-Long Chia、Min-Jen Shiao

  DOI：10.1016/s0040-4039(00)78900-3

  日期：1991.4

  A general approach by use of highly functionalized mixed copper zinc, benzylic organometallics to react with N-ethoxycarbonylpyridinium chloride to give regioselectively 4-benzylpyridines after oxygen oxidation in 30–75% yield is described.

  描述了一种通用方法，该方法是使用高度官能化的混合铜锌，苄基有机金属与N-乙氧基羰基吡啶鎓氯化物反应，经氧氧化后生成区域选择性的4-苄基吡啶，产率为30-75％。
• Regio- and Chemoselective Addition of Mixed Copper, Zinc Benzylic Organometallics to Functionalized Pyridinium Salts: A Facile Synthesis of Functionalized 4-Benzylpyridines
  作者：Tai-Li Shing、Win-Long Chia、Min-Jen Shiao、Tay-Yuan Chau

  DOI：10.1055/s-1991-26589

  日期：——

  2′,3-Disubstituted 4-benzylpyridines 4 were synthesized in good yield by reaction of mixed copper, zinc benzylic organometallics 1 with 3-substituted 1-(ethoxycarbonyl)pyridinium chlorides 2 followed by sulfur oxidation under reflux in decalin.

  合成了2′,3-二取代的4-苄基吡啶4，产率良好，反应是将混合的铜、锌苄基有机金属化合物1与3-取代的1-(乙氧基羧基)吡啶铵盐氯化物2反应，随后在去缪烯中回流氧化硫。
• AKIBA, KIN-YA;ISEKI, YUJI;WADA, MAKOTO, BULL. CHEM. SOC. JAP., 1984, 57, N 7, 1994-1999
  作者：AKIBA, KIN-YA、ISEKI, YUJI、WADA, MAKOTO

  DOI：——

  日期：——