N-(2-bromobenzyl)pyridinium bromide | 13160-93-5

• 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: N-(2-bromobenzyl)pyridinium bromide
• 英文别名: 1-[(2-Bromophenyl)methyl]pyridin-1-ium bromide；1-[(2-bromophenyl)methyl]pyridin-1-ium;bromide
• CAS: 13160-93-5
• 化学式: Br*C₁₂H₁₁BrN
• 分子量: 329.034
• InChiKey: ZPOJSETZYAOVDO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 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：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-bromobenzyl)pyridinium bromide 以 水 为溶剂， 反应 0.33h， 生成 6H-pyrido[2,1-a]isoindolylium bromide
  参考文献：
  名称：

  Park, Y.-T.; Joo, C.-H.; Choi, C.-D., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 1083 - 1089

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴苄醇 在 三溴化磷 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 N-(2-bromobenzyl)pyridinium bromide
  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

• Application of primary halogenated hydrocarbons for the synthesis of 3-aryl and 3-alkyl indolizines
  作者：Yan Liu、Huayou Hu、Junyu Zhou、Wenhui Wang、Youliang He、Chao Wang

  DOI：10.1039/c7ob00980a

  日期：——

  properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-aryl and 3-alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons has been reported

  吲哚利嗪是一种重要的杂环化合物，具有多种令人感兴趣的特性，使其适用于生物学，医学和材料等许多领域的众多应用。然而，尚未报道由庞大的伯卤代烷烃合成3-烷基吲哚嗪。在此，首次报道了利用串联反应从缺电子的烯烃，吡啶和伯卤代烃生成无过渡金属的3-芳基和3-烷基吲哚并嗪的合成路线。该方法的关键步骤是四氢吲哚嗪中间体与2,2,6,6-四甲基哌啶-N的氧化脱氢芳构化-氧基（TEMPO）作为氧化剂。该协议的优势在于它使用易于获得的低成本起始材料，无过渡金属的条件及其可扩展性。
• A One-Pot Domino Reaction for the Synthesis of 3-Arylindolizines from Pyridines, Benzyl Halides, and Dihalide-Substituted Electron-Deficient Alkenes
  作者：Huayou Hu、Kunbo Shi、Rongrong Hou、Zaichao Zhang、Yulan Zhu、Jianfeng Zhou

  DOI：10.1055/s-0030-1258266

  日期：2010.12

  3-Arylindolizines were prepared by one-pot domino reactions from benzyl halides with pyridine (or isoquinoline) and cyclic or acyclic dihalide-substituted electron-deficient alkenes in the presence of potassium carbonate via in situ generated N-ylide intermediate. Both electron-donating and electron-withdrawing groups are tolerated in the aryl ring of benzyl halides. The yields range from moderate to high.

  通过一锅多米诺反应，从苄基卤化物与吡啶（或异喹啉）以及含环状或非环状二卤代取代的缺电子烯烃在碳酸钾存在下，利用原位生成的N-叶立德中间体，制备了3-芳基吲哚啉类化合物。苄基卤化物的芳环上可耐受供电子基团和吸电子基团。产率从中等到高不等。
• Synthesis of Novel Tetrahydrobenzazepine Derivatives and Their Cytoprotective Effect on Human Lymphocytes
  作者：Milena R. Simic、Miroslava Stankovic、Boris M. Mandic、Vele V. Tesevic、Vladimir M. Savic

  DOI：10.1002/ardp.201400350

  日期：2015.2

  based on the privileged tetrahydrobenzazepine scaffold found in many natural products with a wide range of biological properties. This structure was further functionalised with moieties known to possess antioxidative features such as tertiary amine and styrene double bond. A series of eight tetrahydrobenzazepine derivatives of isoquinoline, 3,4‐dihydro‐β‐carboline and pyridine were synthesised employing

  氨磷汀等细胞保护化合物在化疗和放疗中发挥着重要作用，因为它们能够减少这些治疗的副作用。我们的工作旨在设计、合成和测试一类新的杂环化合物，这些化合物具有抗氧化特性，并有可能被进一步开发为细胞保护剂。该设计基于在许多具有广泛生物特性的天然产品中发现的特权四氢苯并氮杂卓支架。该结构进一步被已知具有抗氧化特征的部分官能化，例如叔胺和苯乙烯双键。使用 Heck 反应作为关键转化，合成了一系列八种异喹啉、3,4-二氢-β-咔啉和吡啶的四氢苯并氮杂衍生物。使用细胞松弛素-B 阻断微核 (MN) 测定法测试了一些制备的化合物对外周人淋巴细胞染色体畸变的体外影响。三种四氢苯并氮杂衍生物显示出显着的细胞保护特性，与辐射防护剂氨磷汀相当甚至更好。
• Three-Component Condensation of Pyridinium Ylides, β-Ketonitriles, and Aldehydes with Divergent Regioselectivity: Synthesis of 4,5-Dihydrofuran-3- and 2<i>H</i>-Pyran-5-carbonitriles
  作者：Maxim R. Demidov、Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1021/acs.joc.1c00423

  日期：2021.6.4

  and semistabilized pyridinium ylide precursors, and aldehydes in the presence of piperidine. This one-pot transformation generates two C–C and one C–O bond and proceeds through a cascade Knoevenagel condensation, a Michael addition, and intramolecular SN2 cyclization. Formation of cyclopropanecarbonitrile derivatives, which in some cases were obtained as major products, was found to be a competing

  通过β-酮腈、羰基和半稳定化的吡啶鎓叶立德前体以及醛在哌啶存在下的三组分反应，以非对映选择性方式合成了反式-4,5-二氢呋喃-3-甲腈文库。这种一锅转化生成两个C-C和一个C-O键并经由级联Knoevenagel缩合，迈克尔加成，和分子内小号Ñ 2环化。发现在某些情况下作为主要产物获得的环丙烷甲腈衍生物的形成是一种竞争反应。芳基乙二醛的使用会改变区域选择性并产生 2-hydroxy-2 H - pyran -5-carbonitriles。
• Iodine-Mediated Heterocyclization for the Synthesis of 6-Alkylthio-1,3,5-triazine-2,4-diamines from <i>N</i>-Alkylpyridinium Salts and NH₄SCN
  作者：Zhiqi Liu、Yinghua Li、Weibin Fan、Deguang Huang

  DOI：10.1021/acs.joc.3c02517

  日期：2024.1.5

  An iodine-mediated method for the synthesis of 6-alkylthio-1,3,5-triazine-2,4-diamines by the reaction of N-alkylpyridinium salts and NH4SCN in air is reported. Twenty-seven compounds were obtained under the standard conditions. Pyridinium salts work as benzyl-group transfer reagents to promote the formation of the CBn–SSCN bond and thereby the construction of the triazine skeleton. A plausible mechanism

  报道了一种通过N-烷基吡啶鎓盐与NH 4 SCN在空气中反应合成6-烷硫基-1,3,5-三嗪-2,4-二胺的碘介导方法。在标准条件下获得了27种化合物。吡啶盐作为苄基转移试剂，促进 C Bn –S SCN键的形成，从而构建三嗪骨架。根据实验结果和文献调查，提出了一种合理的机制。