2-(2-bromobenzyl)-1H-indole | 189634-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(2-bromobenzyl)-1H-indole
• 英文别名: 2-[(2-bromophenyl)methyl]-1H-indole
• CAS: 189634-96-6
• 化学式: C₁₅H₁₂BrN
• 分子量: 286.171
• InChiKey: IJDCTWKMQQHYGM-UHFFFAOYSA-N

物化性质

• 沸点：
  430.8±25.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(2-bromobenzyl)-1H-indole 在 potassium phosphate 、 copper(l) iodide 、 trans-1,2-Diaminocyclohexane 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以88%的产率得到10H-indolo[1,2-a]indole
  参考文献：
  名称：

  Divergent synthesis of isoindolo[2,1-a]indole and indolo[1,2-a]indole through copper-catalysed C- and N-arylations

  摘要：

  A simple and efficient synthetic route to both isoindolo[2,1-a]indole and its structural isomer indolo[1,2a]indole skeletons is presented. The key steps of the strategy are based on copper-catalysed C-aryl-C and C-aryl-N bond formation reactions, respectively. Moreover, we report the first copper-mediated intramolecular C-H functionalisation of an indole. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.175
• 作为产物：
  描述：

  2-溴溴苄 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 生成 2-(2-bromobenzyl)-1H-indole
  参考文献：
  名称：

  Facile Synthesis of 2-Benzylindoles

  摘要：

  A wide range of 2-Benzylindoles 2 are conveniently and efficiently prepared by heating N-benzylindoles 1 in polyphosphoric acid. Mechanistic studies suggest an intramolecular rearrangement via the corresponding 3-benzyl intermediates.

  DOI：

  10.1080/00397919708006807

文献信息

• Concise synthesis of cyclic carbonyl compounds from haloarenes using phenyl formate as the carbonyl source
  作者：Hideyuki Konishi、Hiroki Nagase、Kei Manabe

  DOI：10.1039/c4cc09413a

  日期：——

  Carbonylative cyclization of haloarenes bearing nucleophilic moieties under Pd catalysis has been developed as a general, user-friendly method for access to various cyclic carbonyl compounds.

  在钯催化下，含有亲核基团的卤代芳烃的羰基化环化已经发展成为获取各种环状羰基化合物的一种通用、用户友好的方法。

• Synthesis of Fused Polycyclic Indoles by Brønsted Acid-Catalyzed Intramolecular Alkylation of Indoles with Alcohols
  作者：Anisley Suárez、Mukut Gohain、Manuel A. Fernández-Rodríguez、Roberto Sanz

  DOI：10.1021/acs.joc.5b02048

  日期：2015.10.16

  An efficient methodology for the synthesis of a series of new fused polyclyclic indoles has been developed by Brønsted acid-catalyzed intramolecular Friedel–Crafts reactions of properly designed indolyl alcohols.

  通过适当设计的吲哚醇的布朗斯台德酸催化的分子内Friedel-Crafts反应，已开发出一种有效的方法，用于合成一系列新型的熔融聚吲哚。
• Copper-Catalyzed N–H/C–H Sequential Relay Oxidative Radical Carboannulation: Construction of Diversely Substituted [60]Fullerene-Fused Tetrahydrocyclopenta[<i>b</i>]indoles
  作者：Tong-Xin Liu、Juan Wei、Pengling Zhang、Yifei Ru、Jinliang Ma、Xingjie Zhang、Nana Ma、Guisheng Zhang

  DOI：10.1021/acs.orglett.9b02354

  日期：2019.8.16

  carboannulation of [60]fullerene with C2-functionalized free indoles for the direct construction of novel [60]fullerene-fused tetrahydrocyclopenta[b]indoles. The transformation shows high regioselectivity and atom economy, broad substrate scope, and good functional group tolerance, providing an efficient and practical approach to access diversely substituted fullerene-fused polycyclic derivatives from simple

  本文报道了一种新的铜催化的[60]富勒烯与C2官能化的吲哚的铜催化N–H / C–H顺序中继氧化自由基碳环化反应，用于直接构建新颖的[60]富勒烯稠合的四氢环戊[ b ]吲哚。该转化显示出高的区域选择性和原子经济性，广泛的底物范围和良好的官能团耐受性，提供了一种有效且实用的方法来从简单的烃类中获得各种取代的富勒烯稠合的多环衍生物。
• Facile Synthesis of 2-Benzylindoles
  作者：Paul Wiedenau、Siegfried Blechert

  DOI：10.1080/00397919708006807

  日期：1997.6

  A wide range of 2-Benzylindoles 2 are conveniently and efficiently prepared by heating N-benzylindoles 1 in polyphosphoric acid. Mechanistic studies suggest an intramolecular rearrangement via the corresponding 3-benzyl intermediates.
• Divergent synthesis of isoindolo[2,1-a]indole and indolo[1,2-a]indole through copper-catalysed C- and N-arylations
  作者：Nekane Barbero、Raul SanMartin、Esther Domínguez

  DOI：10.1016/j.tetlet.2009.02.175

  日期：2009.5

  A simple and efficient synthetic route to both isoindolo[2,1-a]indole and its structural isomer indolo[1,2a]indole skeletons is presented. The key steps of the strategy are based on copper-catalysed C-aryl-C and C-aryl-N bond formation reactions, respectively. Moreover, we report the first copper-mediated intramolecular C-H functionalisation of an indole. (C) 2009 Elsevier Ltd. All rights reserved.