N,N-dimethyl-2-Methoxycarbonyl-3-(trimethylsilyl)-4-(p-methoxyphenylethynyl)-1H-pyrrole-1-sulfonamide | 221656-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,N-dimethyl-2-Methoxycarbonyl-3-(trimethylsilyl)-4-(p-methoxyphenylethynyl)-1H-pyrrole-1-sulfonamide
• 英文别名: Methyl 1-(dimethylsulfamoyl)-4-[2-(4-methoxyphenyl)ethynyl]-3-trimethylsilylpyrrole-2-carboxylate；methyl 1-(dimethylsulfamoyl)-4-[2-(4-methoxyphenyl)ethynyl]-3-trimethylsilylpyrrole-2-carboxylate
• CAS: 221656-20-8
• 化学式: C₂₀H₂₆N₂O₅SSi
• 分子量: 434.588
• InChiKey: GRXMYAYPOLLYQY-UHFFFAOYSA-N

物化性质

• 熔点：
  115-118 °C
• 沸点：
  568.2±60.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  86.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N,N-dimethyl-2-methoxycarbonyl-3-(trimethylsilyl)-4-(iodoethynyl)-1H-pyrrole-1-sulfonamide 、 4-甲苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.0h， 生成 N,N-dimethyl-2-Methoxycarbonyl-3-(trimethylsilyl)-4-(p-methoxyphenylethynyl)-1H-pyrrole-1-sulfonamide
  参考文献：
  名称：

  PdCl2-catalyzed cross-coupling reaction of arylacetylene iodides with arylboronic acids to diarylacetylenes

  摘要：

  Anew Suzuki-type cross-coupling reaction between 1-iodo-2-arylalkynes and arylboronic acids to afford a wide variety of functionalized diarylacetylenes in a mild reaction condition was developed. The reaction was catalyzed by a small amount of a structurally simple, commercially available, and stable PdCl2. This unique sp-sp(2) carbon-carbon bond formation provides a new protocol for the synthesis of diarylacetylenes, which is a new addition to the Suzuki cross-coupling reaction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.011

文献信息

• Correction to Highly Regioselective Synthesis of 2,3,4-Trisubstituted 1<i>H</i>-Pyrroles: A Formal Total Synthesis of Lukianol A
  作者：Jian-Hui Liu、Qing-Chuan Yang、Thomas C. W. Mak、Henry N. C. Wong

  DOI：10.1021/jo901655y

  日期：2009.9.4

  indicated below (based on the X-ray crystallographic analysis of 19 (Figure 1)). Figure 1. ORTEP (ellipsoids at 50% probability) diagram of 19. Page 3589. “Employing 15a as the starting material, its remaining trimethylsilyl group was again replaced regiospecifically by an iodo group, providing 18 in 82% yield. Finally, Suzuki reaction of 18 with p-methoxybenzeneboronic acid gave the 1-protected 2,3,4-trisubstituted

  Page3589。方案5应该按以下指示进行纠正（基于19的X射线晶体学分析（图1））。图1. ORTEP（在50％的概率椭圆体）的图19。第3589页。“使用15a作为起始原料，其剩余的三甲基甲硅烷基再次被区域特异性地替换为碘基，从而以82％的产率提供18。最后，Suzuki 18与对甲氧基苯硼酸的反应得到了1保护的2,3,4-三取代吡咯19（方案5）。” 应该更正如下：“雇用15a作为起始原料，其末端三键上的三甲基甲硅烷基在区域上被一个碘基取代，提供82％的收率18。最后，Suzuki 18与对甲氧基苯硼酸的反应得到了1保护的2、3、4-三取代的吡咯19（方案5）。” 第3593页。“ N，N-二甲基2-甲氧羰基-3-碘-4-三甲基甲硅烷基乙炔基-1 H-吡咯-1-硫磺酰胺（18）。”应作如下修正：“ N，N-二甲基2-甲氧羰基-3-（三甲基甲硅烷基）-4-（碘乙炔基）-1 H-吡咯-1-磺酰胺（18）。”“
• PdCl2-catalyzed cross-coupling reaction of arylacetylene iodides with arylboronic acids to diarylacetylenes
  作者：Yu Shi、Xiaoyu Li、Jianhui Liu、Wenfeng Jiang、Licheng Sun

  DOI：10.1016/j.tetlet.2010.05.011

  日期：2010.7

  Anew Suzuki-type cross-coupling reaction between 1-iodo-2-arylalkynes and arylboronic acids to afford a wide variety of functionalized diarylacetylenes in a mild reaction condition was developed. The reaction was catalyzed by a small amount of a structurally simple, commercially available, and stable PdCl2. This unique sp-sp(2) carbon-carbon bond formation provides a new protocol for the synthesis of diarylacetylenes, which is a new addition to the Suzuki cross-coupling reaction. (C) 2010 Elsevier Ltd. All rights reserved.