7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-2-(4-isopropoxy-3-methoxyphenyl)-8-methoxy-3-[2-(phenylsulfanyl)ethyl][1]benzopyrano[3,4-b]pyrrol-4(3H)-one | 1519002-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-2-(4-isopropoxy-3-methoxyphenyl)-8-methoxy-3-[2-(phenylsulfanyl)ethyl][1]benzopyrano[3,4-b]pyrrol-4(3H)-one
• 英文别名: 8-Methoxy-2-(3-methoxy-4-propan-2-yloxyphenyl)-1-(4-methoxy-3-propan-2-yloxyphenyl)-3-(2-phenylsulfanylethyl)-7-propan-2-yloxychromeno[3,4-b]pyrrol-4-one；8-methoxy-2-(3-methoxy-4-propan-2-yloxyphenyl)-1-(4-methoxy-3-propan-2-yloxyphenyl)-3-(2-phenylsulfanylethyl)-7-propan-2-yloxychromeno[3,4-b]pyrrol-4-one
• CAS: 1519002-24-4
• 化学式: C₄₃H₄₇NO₈S
• 分子量: 737.914
• InChiKey: PCQAGJCOOASIOV-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  807.1±65.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-2-(4-isopropoxy-3-methoxyphenyl)-8-methoxy-3-[2-(phenylsulfanyl)ethyl][1]benzopyrano[3,4-b]pyrrol-4(3H)-one 在 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 三正丁基氢锡 、 三氯化硼 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.25h， 生成 lamellarin L
  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：

  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 、 sodium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 95.5h， 生成 7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-2-(4-isopropoxy-3-methoxyphenyl)-8-methoxy-3-[2-(phenylsulfanyl)ethyl][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

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.