3-(2,2-dimethoxyethyl)-7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-2-(4-isopropoxy-3-methoxyphenyl)-8-methoxy[1]benzopyrano[3,4-b]pyrrol-4(3H)-one | 1519002-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(2,2-dimethoxyethyl)-7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-2-(4-isopropoxy-3-methoxyphenyl)-8-methoxy[1]benzopyrano[3,4-b]pyrrol-4(3H)-one
• CAS: 1519002-27-7
• 化学式: C₃₉H₄₇NO₁₀
• 分子量: 689.803
• InChiKey: RWEIUHXQVILRSV-UHFFFAOYSA-N

物化性质

• 沸点：
  747.4±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  50.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108.98
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3-(2,2-dimethoxyethyl)-7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-2-(4-isopropoxy-3-methoxyphenyl)-8-methoxy[1]benzopyrano[3,4-b]pyrrol-4(3H)-one 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 以98%的产率得到3,11-diisopropoxy-14-(3-isopropoxy-4-methoxyphenyl)-2,12-dimethoxy-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：

  3-异丙氧基-4-甲氧基苯硼酸 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 、 sodium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 93.5h， 生成 3-(2,2-dimethoxyethyl)-7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-2-(4-isopropoxy-3-methoxyphenyl)-8-methoxy[1]benzopyrano[3,4-b]pyrrol-4(3H)-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