5-溴-2-(4-溴苯基)-1H-吲哚 | 28718-97-0

• 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
• 中文名称: 5-溴-2-(4-溴苯基)-1H-吲哚
• 英文名称: 5-bromo-2-(4-bromophenyl)-1H-indole
• 英文别名: 5-Bromo-2-(4-bromophenyl)-1H-indole
• CAS: 28718-97-0
• 化学式: C₁₄H₉Br₂N
• 分子量: 351.04
• InChiKey: AHJIOTIVIOUCNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 在 aluminum (III) chloride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 2,2,2-三氟乙醇 为溶剂， 反应 54.0h， 生成 5-溴-2-(4-溴苯基)-1H-吲哚
  参考文献：
  名称：

  亲氧路易斯酸促进了乙醇中苯胺和氰基环氧化物合成2-Arylindoles

  摘要：

  在醇中BF 3 ·OEt 2或AlCl 3的催化作用下，开发了一种方便的由苯胺和氰基环氧化物合成吲哚的方法。该反应涉及氰基环氧化物与苯胺的区域特异性开环的串联反应，氰化物的消除，分子内芳族亲电子取代和水的消除。路易斯酸产生的质子酸是有效的催化剂。该方法的特点是易于获得的起始原料，广泛的底物范围，无过渡金属的环境以及氰基环氧化合物开环中的区域特异性。

  DOI：

  10.1021/acs.joc.8b02203

文献信息

• The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons
  作者：Shuling Yu、Linjun Qi、Kun Hu、Julin Gong、Tianxing Cheng、Qingzong Wang、Jiuxi Chen、Huayue Wu

  DOI：10.1021/acs.joc.7b00148

  日期：2017.4.7

  A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations

  首次开发了钯催化的2-（2-氨基芳基）乙腈与芳基硼酸的串联串联加成/环化反应，实现了直接构建吲哚骨架的新策略。该系统显示出良好的官能团耐受性和出色的化学选择性。特别地，卤素（例如，溴和碘）取代基适合于进一步的合成精细化，从而扩大了产物的多样性。初步的机械实验表明，这种转化涉及相继的亲核加成，然后进行分子内环化。
• Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles
  作者：Shuling Yu、Kun Hu、Julin Gong、Linjun Qi、Jianghe Zhu、Yetong Zhang、Tianxing Cheng、Jiuxi Chen

  DOI：10.1039/c7ob00572e

  日期：——

  was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover

  通过在水性介质中钯催化的芳基三氟硼酸钾与脂肪族腈的串联/串联加成/环化反应，开发了构建2-芳基吲哚的有效方案。使用水作为反应介质使合成过程对环境无害。提出了一个合理的机制，形成2-芳基吲哚涉及亲核加成顺序，然后进行分子内环化。此外，这种催化串联转化的效用也在有效的克级合成中得到了证明。该方法提供了另一种可替代的合成工具，可用于获得更多种类的2-芳基吲哚。
• 一种吲哚类化合物的制备方法
  申请人：北京化工大学

  公开号：CN109503454B

  公开（公告）日：2020-09-04

  本发明提供了一种吲哚类化合物的制备方法，2‑氰基环氧乙烷类化合物与芳胺在路易斯酸（三氟化硼乙醚或无水三氯化铝）催化下反应得到相应的吲哚类化合物。该类化合物的制备方法原料简单易得，操作方便，且反应区域选择性专一。所得到的化合物是一类非常重要的有机中间体和药物中间体，具有广泛的生物活性。
• Further investigation of inhibitors of MRSA pyruvate kinase: Towards the conception of novel antimicrobial agents
  作者：Christophe Labrière、Huansheng Gong、B. Brett Finlay、Neil E. Reiner、Robert N. Young

  DOI：10.1016/j.ejmech.2016.09.018

  日期：2017.1

  Several novel series of compounds were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK has been identified as a highly interconnected essential 'hub' protein in MRSA, with structural features distinct from the human homologs which makes it a novel antimicrobial target. Several MRSA PK inhibitors (including the hydrazide 1) were identified using in silico screening combined with enzyme assays and were found to be selective for bacterial enzyme compared to human PK isoforms. Structure-activity relationship (SAR) studies were carried out on the replacement of the hydrazide linker with 3-atoms, 2-atoms and 0-atom linkers and led us to discover more potent compounds with enzyme inhibiting activities in the low nanomolar range and some were found to effectively inhibit bacteria growth in culture with minimum inhibitory concentrations (MIC) as low as 1 mu g/mL. (C) 2016 Elsevier Masson SAS. All rights reserved.