benzyl 2-[(4-acetylphenyl)ethynyl]-5-bromophenylcarbamate | 1315267-69-6

• 英文名称: benzyl 2-[(4-acetylphenyl)ethynyl]-5-bromophenylcarbamate
• CAS: 1315267-69-6
• 化学式: C₂₄H₁₈BrNO₃
• 分子量: 448.316
• InChiKey: YKQWZOLBFVFJIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-[(4-acetylphenyl)ethynyl]-5-bromophenylcarbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以85%的产率得到6-bromo-2-(4-acetylphenyl)-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：

  5-溴-2-碘苯甲酰氯 在 4-二甲氨基吡啶 、 copper(l) iodide 、 sodium azide 、 三(2-呋喃基)膦 、 二异丙胺 、 palladium dichloride 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 4.67h， 生成 benzyl 2-[(4-acetylphenyl)ethynyl]-5-bromophenylcarbamate
  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