Methyl 1-[2-(2-bromophenyl)ethyl]pyrrole-2-carboxylate | 850346-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Methyl 1-[2-(2-bromophenyl)ethyl]pyrrole-2-carboxylate
• CAS: 850346-64-4
• 化学式: C₁₄H₁₄BrNO₂
• 分子量: 308.175
• InChiKey: BVLSFDPYNRFHRN-UHFFFAOYSA-N

物化性质

• 沸点：
  404.8±30.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl 1-[2-(2-bromophenyl)ethyl]pyrrole-2-carboxylate 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 sodium acetate 、 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 Methyl 1,2-bis(4-hydroxyphenyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
  参考文献：
  名称：

  5,6-Dihydropyrrolo[2,1-b]isoquinolines as scaffolds for synthesis of lamellarin analogues

  摘要：

  Efficient modular synthetic routes to open chain marine alkaloids such as lamellarins have been developed. 5,6-Dihydropyrrolo[2, 1-b]isoquinoline scaffolds were prepared, and protocols enabling regioselective bromination followed by Suzuki cross-coupling were established for the introduction of aryl groups onto the 2- and 3-positions. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.145
• 作为产物：
  描述：

  2-溴苯乙醇 在 氢氧化钾 、 18-冠醚-6 、 potassium carbonate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 1-[2-(2-bromophenyl)ethyl]pyrrole-2-carboxylate
  参考文献：
  名称：

  5,6-Dihydropyrrolo[2,1-b]isoquinolines as scaffolds for synthesis of lamellarin analogues

  摘要：

  Efficient modular synthetic routes to open chain marine alkaloids such as lamellarins have been developed. 5,6-Dihydropyrrolo[2, 1-b]isoquinoline scaffolds were prepared, and protocols enabling regioselective bromination followed by Suzuki cross-coupling were established for the introduction of aryl groups onto the 2- and 3-positions. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.145

文献信息

• Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides
  作者：François Bilodeau、Marie-Christine Brochu、Nicolas Guimond、Kris H. Thesen、Pat Forgione

  DOI：10.1021/jo9022793

  日期：2010.3.5

  A full overview of the decarboxylative cross-coupling reaction between heteroaromatic carboxylic acids and aryl halides is described. This transformation employs palladium catalysts with short reaction times providing facile synthesis of aryl-substituted heteroaromatics. The effect of each reaction parameter including solvent, base, and additive employed as well as the full substrate scope of this

  描述了杂芳族羧酸和芳基卤化物之间的脱羧交叉偶联反应的完整概述。该转化采用反应时间短的钯催化剂，可轻松合成芳基取代的杂芳族化合物。报告了每个反应参数的影响，包括所用的溶剂，碱和添加剂，以及该转化的整个底物范围。还公开了机制证据，阐明了可能的反应途径。