1-(2-bromo-ethyl)-quinolinium bromide | 58844-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(2-bromo-ethyl)-quinolinium bromide
• 英文别名: 1-(2-Bromoethyl)quinolinium Bromide；1-(2-bromoethyl)quinolin-1-ium;bromide
• CAS: 58844-03-4
• 化学式: Br*C₁₁H₁₁BrN
• 分子量: 317.023
• InChiKey: RIDWLIMMWZIDGS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.47
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1-(2-bromo-ethyl)-quinolinium bromide 在 manganese(IV) oxide 、 氨 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到imidazo[1,2-a]quinoline
  参考文献：
  名称：

  One-Pot Synthesis of Imidazopyridine Derivatives

  摘要：

  描述了两种高效且通用的一锅法缩合反应，用于合成咪唑并吡啶衍生物（IPs）。这两种程序相辅相成：第一种方法可生产更简单的IPs，而第二种方法则可生成具功能化咪唑基团的IPs。两种方法均包括一个激活步骤，提升N-杂环起始材料的电亲核性（即N-杂环的季铵化），随后进行级联反应，包括亲核加成、取代、重排和氧化步骤。这些方法可用于合成一系列类药物分子。

  DOI：

  10.1055/s-2007-1000936
• 作为产物：
  描述：

  喹啉 、 1,2-二溴乙烷 反应 120.0h， 以95%的产率得到1-(2-bromo-ethyl)-quinolinium bromide
  参考文献：
  名称：

  导致一类N-杂环阳离子扩展的通用一锅三步方法：自发亲核加成，环化和氢化物损失

  摘要：

  从2-溴乙基溴化菲啶鎓与一系列伯胺的反应中已分离出一类新型的菲啶鎓衍生物，收率很高。反应路径是前所未有的，通过三个级联的步骤进行：在杂芳环体系和环化的亚胺部分的伯胺的亲核攻击，以形成一个五元环，随后氢化物损失，得到rearomatized二氢ħ -咪唑并[1,2- f ]菲啶鎓衍生物。进行了一系列NMR相转移实验以阐明机理途径，并且该方法已经通过使用N-溴代琥珀酰亚胺作为助氧化剂的双相系统进一步发展。该方法也已扩展到其他N-杂环阳离子衍生物，例如喹啉鎓和喹唑啉鎓。

  DOI：

  10.1021/jo0495440

文献信息

• 3-Halo-cepham derivatives
  申请人：American Home Products Corporation

  公开号：US03932398A1

  公开（公告）日：1976-01-13

  Penicillin sulfoxides are converted to 3-halo-3-methyl-cepham-4-carboxylic acid esters and amides or the corresponding cephem derivatives by heating the penicillin sulfoxide precursor in a polyhaloalkane solvent to a temperature between 50.degree. to about 150.degree.C. in the presence of an equimolar amount of a neutral or basic catalyst, respectively. The catalysts employed are bases such as pyridine, picoline, lutidine, quinoline, isoquinoline, dimethylaniline or a quaternary ammonium salt. The 3-halo-cepham intermediates produced with a quaternary ammonium catalyst are dehydrohalogenated to afford known cephem derivatives or converted to the free 4-carboxylic acid and the alkali metal, alkaline earth metal or ammonium salts thereof to afford novel antibacterial agents.

  青霉素亚砜可以在多卤代烷溶剂中加热其前体，与中性或碱性催化剂反应，分别转化为3-卤代-3-甲基-头孢四烯-4-羧酸酯和酰胺或相应的头孢菌素衍生物。所使用的催化剂为碱性物质，如吡啶、吡啶甲醛、卢田、喹啉、异喹啉、二甲基苯胺或季铵盐。使用季铵盐催化剂产生的3-卤代头孢中间体被脱卤化以得到已知的头孢菌素衍生物，或者转化为自由的4-羧酸和碱金属、碱土金属或铵盐，以制备新的抗菌剂。
• Process for the rearrangement of penicillins to cephalosporins and
  申请人：American Home Products Corporation

  公开号：US04010156A1

  公开（公告）日：1977-03-01

  Penicillin sulfoxides are converted to 3-halo-3-methyl-cepham-4-carboxylic acid esters and amides or the corresponding cephem derivatives by heating the penicillin sulfoxide precursor in a polyhaloalkane solvent to a temperature between 50.degree. to about 150.degree. C. in the presence of an equimolar amount of a neutral or basic catalyst, respectively. The catalysts employed are bases such as pyridine, picoline, lutidine, quinoline, isoquinoline, dimethylaniline or a quaternary ammonium salt. The 3-halo-cepham intermediates produced with a quaternary ammonium catalyst are dehydrohalogenated to afford known cephem derivatives or converted to the free 4-carboxylic acid and the alkali metal, alkaline earth metal or ammonium salts thereof to afford novel antibacterial agents.

  青霉素亚磺酸酯经在多卤代烷溶剂中，在50度至约150度C的温度下，在中性或碱性催化剂的存在下，分别转化为3-卤代-3-甲基-头孢四烯-4-羧酸酯和酰胺或相应的头孢菌素衍生物。所使用的催化剂是碱性物质，如吡啶、哌啶、戊啶、喹啉、异喹啉、二甲基苯胺或季铵盐。用季铵盐催化剂产生的3-卤代-头孢烯中间体经脱卤化反应，得到已知的头孢菌素衍生物或转化为自由的4-羧酸和碱金属、碱土金属或铵盐，从而得到新的抗菌剂。
• Phenanthridinium Derivatives as Dna Binding Agents
  申请人：Parenty Alexis

  公开号：US20070249652A1

  公开（公告）日：2007-10-25

  New classes of heterocyclic aromatic cationic compounds are disclosed, and in particular new classes of phenanthridinium derivatives, most notably dihydro-imidazo-phenanthridinium (DIP) compounds. These findings are based on the reaction of the middle b ring of a phenanthridinium core with primary amines to form DIP compounds (Formula A) or secondary amines to form 2-aminoalkyl phenanthridinium derivatives (Formula B). These reactions can also be applied to other classes of starting compounds which comprise a 6-membered ring aromatic heterocycle having a ring nitrogen and at least one alpha hydrogen atom which can be reacted with a primary or secondary amine.

  本文披露了一类新的杂环芳香阳离子化合物，特别是新的苯并咪唑苯并三氮杂环（DIP）化合物。这些发现基于苯并三氮杂环核心的中间b环与一级胺反应形成DIP化合物（公式A）或二级胺反应形成2-氨基烷基苯并三氮杂环衍生物（公式B）。这些反应也可以应用于其他类似的起始化合物，其包含一个具有环氮和至少一个α-氢原子的6元环芳香杂环，可以与一级或二级胺反应。
• Copper-Catalyzed Oxidative C–H Annulation of Quinolines with Dichloroethane toward Benzoquinoliziniums Using an In Situ Activation Strategy
  作者：Jinwen Ji、Linfeng Jiang、Zhishuo Wang、Zhengyang Bin、Jingsong You、Yudong Yang

  DOI：10.1021/acs.orglett.2c02342

  日期：2022.9.2

  Described herein is a copper-catalyzed oxidative C–H annulation of quinolines with 1,2-chloroethane (DCE), providing a concise synthetic approach to benzoquinoliziniums. In this protocol, DCE not only serves as a solvent and an in situ activation agent of quinoline C2–H but also works as vinyl equivalents to constitute the six-membered azonia ring. Furthermore, the resultant benzoquinolizinium library

  本文描述的是喹啉与 1,2-氯乙烷 (DCE) 的铜催化氧化 C-H 环化，为苯并喹啉鎓提供了一种简洁的合成方法。在该协议中，DCE 不仅作为溶剂和喹啉 C2-H 的原位活化剂，而且还作为乙烯基等价物构成六元氮环。此外，所得苯并喹啉鎓文库表现出良好的DNA结合特性和低细胞毒性。
• An unusual substitution reaction directed by an intramolecular re-arrangement
  作者：Alexis D.C. Parenty、Louise V. Smith、Leroy Cronin

  DOI：10.1016/j.tet.2005.06.074

  日期：2005.8

  Secondary amines and thiols undertake a substitution reaction on the side chain of 2-bromoethyl-pyridinium derivatives ' directed ' by an intramolecular re-arrangement. Experimental investigations strongly indicate that the reaction is initiated by an alpha addition of the nucleophile onto the iminium moiety of the N-heteroaromatic cation, followed by a cyclisation and in oxidative ring opening. This novel substitution process is able to occur with less reactive nucleophiles that would not undergo conventional substitution with ' isolated ' bromoethyl moieties. (c) 2005 Elsevier Ltd. All rights reserved.