benzyl 5-bromo-2-iodophenylcarbamate | 1315267-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 5-bromo-2-iodophenylcarbamate
• 英文别名: benzyl N-(5-bromo-2-iodophenyl)carbamate
• CAS: 1315267-65-2
• 化学式: C₁₄H₁₁BrINO₂
• 分子量: 432.055
• InChiKey: ANIHYKJZQHLOBM-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  415.0±45.0 °C(Predicted)
• 密度：
  1.896±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl 5-bromo-2-iodophenylcarbamate 在 copper(l) iodide 、 三(2-呋喃基)膦 、 四丁基氟化铵 、 二异丙胺 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成 6-bromo-2-(4-nitrophenyl)-1H-indole
  参考文献：
  名称：

  Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

  摘要：

  The synthesis of 6-bromo-2-arylindoles starting from readily available 2-iodobenzoic acid is presented. Regioselective bromination of the latter was followed by Curtius rearrangement and trapping of the isocyanate with benzyl alcohol led to the benzyl carbamate of 2-iodo-5-bromoaniline. Chemoselective Sonogashira coupling of this compound with arylacetylenes followed by TBAF induced 5-endo-dig cyclization gave the desired bromo indoles. The method allows selective introduction of a bromine atom at the indole C-6 position. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.040
• 作为产物：
  描述：

  2-碘苯甲酸 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 sodium azide 、 硫酸 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 5.67h， 生成 benzyl 5-bromo-2-iodophenylcarbamate
  参考文献：
  名称：

  Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

  摘要：

  The synthesis of 6-bromo-2-arylindoles starting from readily available 2-iodobenzoic acid is presented. Regioselective bromination of the latter was followed by Curtius rearrangement and trapping of the isocyanate with benzyl alcohol led to the benzyl carbamate of 2-iodo-5-bromoaniline. Chemoselective Sonogashira coupling of this compound with arylacetylenes followed by TBAF induced 5-endo-dig cyclization gave the desired bromo indoles. The method allows selective introduction of a bromine atom at the indole C-6 position. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.040

文献信息

• Synthesis and photophysical properties of highly fluorescent 2-aryl-6-(aryleneethynylene)-1H-indoles
  作者：Mariana Flores-Jarillo、Alejandro Alvarez-Hernandez、Rosa Ángeles Vazquez-García、Eduardo Arias、Ivana Moggio、José Román Torres

  DOI：10.1016/j.dyepig.2016.05.017

  日期：2016.10

  cross-coupling in DMSO and fluoride promoted cyclization followed by N-alkylation. The photophysical properties of these compounds are described. Absorption and excitation spectra of these compounds were independent of the solvent polarity, while their emission spectra showed a pronounced dependence. Fluorescence quantum yields in solution were very high and decreased with solvent polarity; possible processes that

  通过在DMSO中一锅Sonogashira交叉偶联和氟化物促进的环化，然后进行N-烷基化，制备了九种新颖的2-芳基-6-（亚芳基乙炔基）-1 H-吲哚。描述了这些化合物的光物理性质。这些化合物的吸收和激发光谱与溶剂极性无关，而它们的发射光谱显示出明显的依赖性。溶液中的荧光量子产率很高，并且随着溶剂极性的降低而降低。讨论了导致excessive的值过大的可能过程。循环伏安法研究表明不可逆的氧化还原过程，DFT计算表明它们发生在吲哚段。