10H-indolo[1,2-a]indole | 206-79-1

• 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: 10H-indolo[1,2-a]indole
• 英文别名: 10H-indolo[2,1-a]indole
• CAS: 206-79-1
• 化学式: C₁₅H₁₁N
• 分子量: 205.259
• InChiKey: STRSWNIAHHUMPB-UHFFFAOYSA-N

物化性质

• 沸点：
  359.0±30.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)
• 熔点：
  52-53 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  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

文献信息

• Palladium-Catalyzed Formal [4 + 1] Annulation via Metal Carbene Migratory Insertion and C(sp²)–H Bond Functionalization
  作者：Shuai Xu、Ri Chen、Zihao Fu、Qi Zhou、Yan Zhang、Jianbo Wang

  DOI：10.1021/acscatal.6b03562

  日期：2017.3.3

  A highly efficient and operationally simple palladium-catalyzed formal [4 + 1] annulation reaction has been developed. The reaction is featured by the formation of two different C–C bonds on a carbenic center. It represents a concise method for the synthesis of a wide range of polycyclic aromatic hydrocarbons (PAHs) and 1H-indenes with easily available (trimethylsilyl)diazomethane as the carbene source

  已经开发出了一种高效且操作简单的钯催化的正[4 +1]环化反应。该反应的特征是在羧基中心上形成两个不同的C–C键。它代表了一种简便的方法，用于合成多种多环芳烃（PAH）和1 H-茚，并以易于获得的（三甲基甲硅烷基）重氮甲烷作为卡宾源。金属卡宾迁移插入和C（sp 2）–H键活化被提议为该转变的关键步骤。该反应进一步证明了与各种过渡金属催化的转化结合的基于卡宾的偶联的多功能性。
• [EN] NOVEL INDICATOR PLATFORM<br/>[FR] NOUVELLE PLATEFORME INDICATRICE
  申请人：BIOSYNTH AG

  公开号：WO2010128120A1

  公开（公告）日：2010-11-11

  A novel indicator platform comprises a plurality of 1 H-lndol-3-yl indicator compounds that are capable of converting to a signalophore compound in response to an external stimulus. In one class of indicator compounds, the resulting signalophores are 2-benzylideneindoline compounds that are formed by an intermolecular Aldol-type process; in a further class of indicator compounds, the resulting signalophores are 10H-indolo[1,2-a]indole compounds that are formed by an intramolecular Aldol-type process. The indicators can be used in a wide array of applications relating, for example, to biological systems or optical data storage.

  一种新颖的指示剂平台包括多种1H-吲哚-3-基指示化合物，这些化合物能够在外部刺激作用下转化为信号体化合物。在一类指示化合物中，产生的信号体是通过分子间Aldol型过程形成的2-苄基亚甲基吲哚化合物；在另一类指示化合物中，产生的信号体是通过分子内Aldol型过程形成的10H-吲哚[1,2-a]吲哚化合物。这些指示剂可用于涉及生物系统或光学数据存储等各种应用中。
• MATERIALS FOR ELECTRONIC DEVICES
  申请人：Mujica-Fernaud Teresa

  公开号：US20140027755A1

  公开（公告）日：2014-01-30

  The present invention relates to an electronic device comprising one or more compounds of a formula (I) or (II). Furthermore, the invention encompasses the use of a compound of the formula (I) or (II) in an electronic device, and the provision of certain compounds of the formula (I) or (II).

  本发明涉及一种电子设备，其包括一个或多个公式(I)或(II)的化合物。此外，本发明还涵盖了在电子设备中使用公式(I)或(II)的化合物，以及提供公式(I)或(II)的某些化合物。
• Novel indicator platform
  申请人：Biosynth AG

  公开号：EP2256103A1

  公开（公告）日：2010-12-01

  A novel indicator platform comprises a plurality of 1H-Indol-3-yl indicator compounds that are capable of converting to a signalophore compound in response to an external stimulus. In one class of indicator compounds, the resulting signalophores are 2-benzylideneindoline compounds that are formed by an intermolecular Aldol-type process; in a further class of indicator compounds, the resulting signalophores are 10H-indolo[1,2-a]indole compounds that are formed by an intramolecular Aldol-type process. The indicators can be used in a wide array of applications relating, for example, to biological systems or optical data storage.

  一种新型指示剂平台由多种 1H-吲哚-3-基指示剂化合物组成，这些化合物能够在外部刺激下转化为信号团化合物。在一类指示剂化合物中，产生的信号团是通过分子间醛醇型过程形成的 2-亚苄基吲哚啉化合物；在另一类指示剂化合物中，产生的信号团是通过分子内醛醇型过程形成的 10H-吲哚并[1,2-a]吲哚化合物。这些指示剂可广泛应用于生物系统或光学数据存储等领域。
• Novel indicator compounds
  申请人：Biosynth AG

  公开号：EP2453021A1

  公开（公告）日：2012-05-16

  A novel class of chromogenic and fluorogenic indicators responding to external stimuli such as biochemical environment, temperature or photo irradiation comprises a plurality of compounds that are converted by an intramolecular aldol condensation to corresponding 10H-indolo[1,2-a]indole of (5H,7H)-indolo[1,2-a]quinoline signalophores. The indicators offer broad potential in a wide array of applications, particularly for biological systems.

  一类对生化环境、温度或光照等外部刺激做出反应的新型发色和发荧光指示剂由多种化合物组成，这些化合物通过分子内醛缩合转化为相应的 10H-吲哚并[1,2-a]吲哚的 (5H,7H)-吲哚并[1,2-a]喹啉信号团。这些指示剂具有广泛的应用潜力，尤其适用于生物系统。