5-(2-piperidin-1-yl-ethyl)-phenanthridinium bromide

• 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: 5-(2-piperidin-1-yl-ethyl)-phenanthridinium bromide
• 英文别名: 5-(2-Piperidin-1-ylethyl)phenanthridin-5-ium;bromide
• 化学式: Br*C₂₀H₂₃N₂
• 分子量: 371.32
• InChiKey: AFBJCLHQYSQKHN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  7.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  菲啶 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168048.0h， 生成 5-(2-piperidin-1-yl-ethyl)-phenanthridinium bromide
  参考文献：
  名称：

  An unusual substitution reaction directed by an intramolecular re-arrangement

  摘要：

  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.

  DOI：

  10.1016/j.tet.2005.06.074

文献信息

• 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。
• [EN] PHENANTHRIDINIUM DERIVATIVES AS DNA BINDING AGENTS<br/>[FR] COMPOSES AROMATIQUES HETEROCYCLIQUES
  申请人：UNIV GLASGOW

  公开号：WO2005054241A3

  公开（公告）日：2005-07-28
• PHENANTHRIDINIUM DERIVATIVES AS DNA BINDING AGENTS
  申请人：University Court of The University of Glasgow

  公开号：EP1692130B1

  公开（公告）日：2007-08-08
• US7947703B2
  申请人：——

  公开号：US7947703B2

  公开（公告）日：2011-05-24
• 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.