3-(3-Aminopropyl)-1,1,2-trimethylbenz(e)indolium bromide.HBr | 162411-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(3-Aminopropyl)-1,1,2-trimethylbenz(e)indolium bromide.HBr
• 英文别名: 3-(1,1,2-Trimethylbenzo[e]indol-3-ium-3-yl)propan-1-amine;bromide;hydrobromide
• CAS: 162411-26-9
• 化学式: BrH*Br*C₁₈H₂₃N₂
• 分子量: 428.21
• InChiKey: DKTDKOQHPGCPJH-UHFFFAOYSA-M

物化性质

• 熔点：
  246-249 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  3-(3-Aminopropyl)-1,1,2-trimethylbenz(e)indolium bromide.HBr 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以50%的产率得到10a,11,11-trimethyl-7,8,9,10,10a,11-hexahydro-6b,10-diaza-benzo[a]fluorene
  参考文献：
  名称：

  Latent fluorophores based on a Mannich cyclisation trigger

  摘要：

  We report the synthesis of a strongly blue-fluorescent pyrazino-benz[e]indole derivative, and its utility for enzyme sensing in biological assays through an original Mannich cyclisation triggered fluorescence unveiling. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.138
• 作为产物：
  描述：

  1,1,2-三甲基苯-1H-苯并[e]吲哚 、 3-溴丙胺氢溴酸盐 反应 10.0h， 以93%的产率得到3-(3-Aminopropyl)-1,1,2-trimethylbenz(e)indolium bromide.HBr
  参考文献：
  名称：

  A New Method for the Synthesis of Heptamethine Cyanine Dyes: Synthesis of New Near-Infrared Fluorescent Labels

  摘要：

  A new uncatalyzed synthesis of heptamethine cyanine dyes is described. The reaction involves heating a mixture of N-alkyl-substituted quaternary salts derived from 2,3,3-trimethylindole or 2,3,3-trimethylbenzindole and 2-chloro-1-formyl-3-(hydroxymethylene)cyclohex-1-ene to reflux in a mixture of 1-butanol and benzene (7:3) as solvent. No catalyst is used, and water is removed as an azeotrope. The resulting chloro compounds possess strong absorption and fluorescence properties in the near-infrared region and are converted to dyes bearing reactive functionalities such as hydroxy and isothiocyanate groups useful as fluorescent tags for nucleic acids and proteins. Several symmetric and nonsymmetric dyes have been synthesized in high yields.

  DOI：

  10.1021/jo00113a018

文献信息

• A New Method for the Synthesis of Heptamethine Cyanine Dyes: Synthesis of New Near-Infrared Fluorescent Labels
  作者：Narasimhachari Narayanan、Gabor Patonay

  DOI：10.1021/jo00113a018

  日期：1995.4

  A new uncatalyzed synthesis of heptamethine cyanine dyes is described. The reaction involves heating a mixture of N-alkyl-substituted quaternary salts derived from 2,3,3-trimethylindole or 2,3,3-trimethylbenzindole and 2-chloro-1-formyl-3-(hydroxymethylene)cyclohex-1-ene to reflux in a mixture of 1-butanol and benzene (7:3) as solvent. No catalyst is used, and water is removed as an azeotrope. The resulting chloro compounds possess strong absorption and fluorescence properties in the near-infrared region and are converted to dyes bearing reactive functionalities such as hydroxy and isothiocyanate groups useful as fluorescent tags for nucleic acids and proteins. Several symmetric and nonsymmetric dyes have been synthesized in high yields.
• Latent fluorophores based on a Mannich cyclisation trigger
  作者：Guillaume Clavé、Aude Bernardin、Marc Massonneau、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1016/j.tetlet.2006.06.138

  日期：2006.8

  We report the synthesis of a strongly blue-fluorescent pyrazino-benz[e]indole derivative, and its utility for enzyme sensing in biological assays through an original Mannich cyclisation triggered fluorescence unveiling. (c) 2006 Elsevier Ltd. All rights reserved.