1-benzyl-3-hydroxypyridinium bromide | 62214-78-2

• 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: 1-benzyl-3-hydroxypyridinium bromide
• 英文别名: 1-benzyl-3-hydroxypyridin-1-ium bromide；1-benzylpyridin-1-ium-3-ol;bromide
• CAS: 62214-78-2
• 化学式: Br*C₁₂H₁₂NO
• 分子量: 266.137
• InChiKey: JIOVVLHSCLWWBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.27
• 重原子数：
  15
• 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：
  24.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-hydroxypyridinium bromide 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成 8-benzyl-6-(phenylsulfonyl)-8-azabicyclo[3.2.1]oct-3-en-2-one
  参考文献：
  名称：

  Structure of the Calystegines: New alkaloids of the nortropane family.

  摘要：

  DOI：

  10.1016/s0040-4039(00)97494-x
• 作为产物：
  描述：

  3-羟基吡啶 、 溴甲苯 以 丙醇 为溶剂， 生成 1-benzyl-3-hydroxypyridinium bromide
  参考文献：
  名称：

  通过1,3-偶极环加成反应固相合成功能化的托烷衍生物

  摘要：

  3-氧化吡啶鎓甜菜碱在固相上的活化烯烃上的1,3-偶极环加成反应会导致树脂结合的8-氮杂双环[3.2.1]辛烯酮发生进一步的转化，例如亲核试剂的1,4-加成。在碘化钾存在下，使用酰氯实现苄基连接基的裂解，得到取代的托烷衍生物。

  DOI：

  10.1016/s0040-4039(01)00565-2

文献信息

• Efficient and Chemoselective Reduction of Pyridines to Tetrahydropyridines and Piperidines<i>via</i>Rhodium-Catalyzed Transfer Hydrogenation
  作者：Jianjun Wu、Weijun Tang、Alan Pettman、Jianliang Xiao

  DOI：10.1002/adsc.201201034

  日期：2013.1.14

  [Cp*RhCl2]2, catalyzes efficiently the transfer hydrogenation of various quaternary pyridinium salts under mild conditions, affording not only piperidines but also 1,2,3,6‐tetrahydropyridines in a highly chemoselective fashion, depending on the substitution pattern at the pyridinium ring. The reduction is conducted in azeotropic formic acid/triethylamine (HCOOH‐Et3N) mixture at 40 °C, with catalyst loadings

  在碘化物阴离子的作用下，铑络合物二聚体[Cp * RhCl 2 ] 2在温和的条件下有效催化各种季铵盐的转移氢化，不仅提供哌啶，而且还提供高度化学选择性的1,2,3,6-四氢吡啶取决于吡啶环上的取代方式。还原反应是在40°C的共沸甲酸/三乙胺（HCOOH-Et 3 N）混合物中进行的，催化剂负载量低至0.005 mol％是可行的。
• Synthesis and evaluation of the performance of a small molecule library based on diverse tropane-related scaffolds
  作者：Robert A. Lowe、Dale Taylor、Kelly Chibale、Adam Nelson、Stephen P. Marsden

  DOI：10.1016/j.bmc.2020.115442

  日期：2020.5

  to the key bicyclic intermediates. A set of 53 screening compounds was designed, synthesised and evaluated in order to determine the biological relevance of the scaffolds accessible using the synthetic approach. Two inhibitors of Hedgehog signalling, and four compounds with weak activity against the parasite P. falciparum, were discovered. Three of the active compounds may be considered to be indotropane

  开发了一种统一的合成方法，可以合成多种与托烷相关的支架。开发的关键中间体是3-羟基吡啶鎓盐与乙烯基砜或磺酰胺之间反应形成的环加合物。通过将取代基添加到关键的双环中间体上，进行环化反应以及将额外的环与所述稠合的双环中间体融合，从而形成了多种与托烷相关的支架。设计，合成和评估了一组53种筛选化合物，以确定使用合成方法可接近的支架的生物学相关性。两种刺猬信号抑制剂和四种对恶性疟原虫的活性较弱的化合物，被发现。可以将其中的三种活性化合物视为吲哚环烷或吡咯烷假的天然产物，其中的托烷与另一种天然产物的片段融合在一起。结论是，统一的合成方法产生了适用于性能多样化筛选文库设计的多种支架。
• Substituted pyridine compounds useful as modulators of acetylcholine receptors
  申请人：Merck & Co., Inc.

  公开号：US06632823B1

  公开（公告）日：2003-10-14

  In accordance with the present invention, a novel class of substituted pyridine compounds (optionally containing ether, ester, amide, ketone or thioether substitutions) that promote the release of ligands involved in neurotransmission have been discovered. In a particular aspect compounds of the present invention are capable of modulating acetylcholine receptors. The compounds of the present invention are capable of modulating acetylcholine receptors. Invention compounds may act as agonists, partial agonists, antagonists or allosteric modulators of acetylcholine receptors. Therapeutic indications for compounds with activity at acetylcholine receptors include diseases of the central nervous system such as Alzheimer's disease and other diseases involving memory loss and/or dementia (including AIDS dementia); cognitive dysfunction (including disorders of attention, focus and concentration), disorders of extrapyramidal motor function such as Parkinson's disease, progressive supramuscular palsy, Huntington's disease, Gilles de la Tourette syndrome and tardive dyskinesia; mood and emotional disorders such as depression, anxiety and psychosis; substance abuse including withdrawal symptoms and substitution therapy; neurocrine disorders and dysregulation of food intake, including bulimia and anorexia; disorders or nociception and control of pain; autonomic disorders including dysfunction of gastrointestinal motility and function such as inflammatory bowel disease, irritable bowel syndrome, diarrhea, constipation, gastric acid secretion and ulcers; pheochromocytoma, cardiovascular dysfunction including hypertension and cardiac arrhythmias, as well as co-medication uses in surgical applications.

  根据本发明，发现了一类新型的取代吡啶化合物（可选地含有醚、酯、酰胺、酮或硫醚取代基），这些化合物促进了神经递质释放所涉及的配体。在特定方面，本发明的化合物能够调节乙酰胆碱受体。本发明的化合物能够调节乙酰胆碱受体。发明化合物可能作为乙酰胆碱受体的激动剂、部分激动剂、拮抗剂或变构调节剂。具有对乙酰胆碱受体活性的化合物的治疗适应症包括中枢神经系统疾病，如阿尔茨海默病和其他涉及记忆丧失和/或痴呆的疾病（包括艾滋病痴呆）；认知功能障碍（包括注意力、集中力和注意力障碍的疾病）；外囊运动功能障碍，如帕金森病、进行性肌肉萎缩性侧索硬化、亨廷顿病、吉尔·德·拉·图雷特综合征和迟发性运动障碍；情绪和情感障碍，如抑郁症、焦虑和精神病；物质滥用，包括戒断症状和替代疗法；神经内分泌紊乱和食物摄入调节失调，包括暴食症和厌食症；疼痛感知和疼痛控制障碍；自主神经功能障碍，包括胃肠道蠕动和功能障碍，如炎症性肠病、肠易激综合征、腹泻、便秘、胃酸分泌和溃疡；嗜铬细胞瘤，心血管功能障碍，包括高血压和心律失常，以及在外科应用中的联合用药。
• 1,3-Dipolar character of six-membered aromatic rings. Part 52. 2π+ 8π Cycloaddition reactions of 1-substituted 3-oxidopyridinium betaines
  作者：Alan R. Katritzky、Alan T. Cutler、Nicholas Dennis、Gebran J. Sabongi、Soheila Rahimi-Rastgoo、Gerhard W. Fischer、Ian J. Fletcher

  DOI：10.1039/p19800001176

  日期：——

  Dichloroketen and a series of aryl(bromo)ketens react with various 1-substituted 3-oxidopyridiniums to give novel bicyclic compounds by addition across the C(4)–O and the C(2)–O positions. Frontier-MO theory is used to rationalise the orientation of these cycloadditions. Acid-catalysed hydrolysis of the C(2)–O adducts (9) yielded 3-hydroxy-2-benzylpyridines.

  二氯酮和一系列芳基（溴）酮与各种1-取代的3-氧化吡啶鎓反应，通过在C（4）–O和C（2）–O位置加成生成新型双环化合物。Frontier-MO理论用于合理化这些环加成的方向。酸催化的C（2）-O加合物（9）水解产生3-羟基-2-苄基吡啶。
• Iridium-Catalyzed Selective Hydrogenation of 3-Hydroxypyridinium Salts: A Facile Synthesis of Piperidin-3-ones
  作者：Wen-Xue Huang、Bo Wu、Xiang Gao、Mu-Wang Chen、Baomin Wang、Yong-Gui Zhou

  DOI：10.1021/acs.orglett.5b00276

  日期：2015.4.3

  homogeneous iridium catalyst, providing a direct access to 2- and 4-substituted piperidin-3-one derivatives with high yields, which are important organic synthetic intermediates and the prevalent structural motifs in pharmaceutical agents. Mild reaction conditions, high chemoselectivity, and easy scalability make this reaction highly practical for the synthesis of piperidin-3-ones.

  已经使用均相铱催化剂实现了3-羟基吡啶鎓盐的选择性加氢，可以高产率直接获得2-和4-取代的哌啶-3-酮衍生物，这些衍生物是重要的有机合成中间体，并且在结构上很普遍。药剂。温和的反应条件，高的化学选择性和容易的可扩展性使该反应在合成哌啶3-3-酮中具有很高的实用性。