methyl 5-(4-isopropoxy-3-methoxyphenyl)-1H-pyrrole-2-carboxylate | 1519002-13-1

• 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 5-(4-isopropoxy-3-methoxyphenyl)-1H-pyrrole-2-carboxylate
• 英文别名: methyl 5-(3-methoxy-4-propan-2-yloxyphenyl)-1H-pyrrole-2-carboxylate
• CAS: 1519002-13-1
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: MMZXLVPPDHLEEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-(4-isopropoxy-3-methoxyphenyl)-1H-pyrrole-2-carboxylate 在 1,1'-双(二苯基膦)二茂铁 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 三氟甲磺酸三甲基硅酯 、 sodium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.75h， 生成 3,11-diisopropoxy-14-(3-isopropoxy-4-methoxyphenyl)-2,12-dimethoxy-9-(phenylsulfanyl)-8,9-dihydro-6H-[1]-benzopyrano[4′,3′:4,5]pyrrolo[2,1-a]isoquinolin-6-one
  参考文献：
  名称：

  Modular Synthesis of Lamellarins via Regioselective Assembly of 3,4,5-Differentially Arylated Pyrrole-2-carboxylates

  摘要：

  A modular synthesis of lamellarins via 3,4,5-differentially arylated pyrrole-2-carboxylate intermediates has been developed. The key reactions employed are Br-Li exchange-methoxycarbonylation of 2,5-dibromo-1-(tert-butoxycarbonyl)-1H-pyrrole (1) followed by palladium-catalyzed iterative Suzuki-Miyaura coupling of the pyrrole core. The 3,4,5-triarylpyrrole 4 thus synthesized was readily converted to 5,6-saturated lamellarin L (2) and 5,6-unsaturated lamellarin N (3) via lactonization followed by annulation of the pyrrole nitrogen and lateral aromatic ring at C5 using 2-bromoethyl phenyl sulfide or bromoacetaldehyde dimethyl acetal as two-carbon homologation agents. In principle, this strategy allows the production of diverse lamellarins in short steps with high yields using readily accessible arylboronic acids as aromatic modules.

  DOI：

  10.1021/jo402181w
• 作为产物：
  描述：

  4-isopropoxy-3-methoxyphenylboronic acid 、 5-溴-1-(1,1-二甲基乙基)-1H-吡咯-1,2-二羧酸-2-甲酯 在 四(三苯基膦)钯 、 sodium carbonate 、 甲醇 、 sodium 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 40.5h， 以2.52 g的产率得到methyl 5-(4-isopropoxy-3-methoxyphenyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Modular Synthesis of Lamellarins via Regioselective Assembly of 3,4,5-Differentially Arylated Pyrrole-2-carboxylates

  摘要：

  A modular synthesis of lamellarins via 3,4,5-differentially arylated pyrrole-2-carboxylate intermediates has been developed. The key reactions employed are Br-Li exchange-methoxycarbonylation of 2,5-dibromo-1-(tert-butoxycarbonyl)-1H-pyrrole (1) followed by palladium-catalyzed iterative Suzuki-Miyaura coupling of the pyrrole core. The 3,4,5-triarylpyrrole 4 thus synthesized was readily converted to 5,6-saturated lamellarin L (2) and 5,6-unsaturated lamellarin N (3) via lactonization followed by annulation of the pyrrole nitrogen and lateral aromatic ring at C5 using 2-bromoethyl phenyl sulfide or bromoacetaldehyde dimethyl acetal as two-carbon homologation agents. In principle, this strategy allows the production of diverse lamellarins in short steps with high yields using readily accessible arylboronic acids as aromatic modules.

  DOI：

  10.1021/jo402181w

文献信息

• Modular Synthesis of Lamellarins via Regioselective Assembly of 3,4,5-Differentially Arylated Pyrrole-2-carboxylates
  作者：Masashi Komatsubara、Teppei Umeki、Tsutomu Fukuda、Masatomo Iwao

  DOI：10.1021/jo402181w

  日期：2014.1.17

  A modular synthesis of lamellarins via 3,4,5-differentially arylated pyrrole-2-carboxylate intermediates has been developed. The key reactions employed are Br-Li exchange-methoxycarbonylation of 2,5-dibromo-1-(tert-butoxycarbonyl)-1H-pyrrole (1) followed by palladium-catalyzed iterative Suzuki-Miyaura coupling of the pyrrole core. The 3,4,5-triarylpyrrole 4 thus synthesized was readily converted to 5,6-saturated lamellarin L (2) and 5,6-unsaturated lamellarin N (3) via lactonization followed by annulation of the pyrrole nitrogen and lateral aromatic ring at C5 using 2-bromoethyl phenyl sulfide or bromoacetaldehyde dimethyl acetal as two-carbon homologation agents. In principle, this strategy allows the production of diverse lamellarins in short steps with high yields using readily accessible arylboronic acids as aromatic modules.