7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-2-(4-isopropoxy-3-methoxyphenyl)-8-methoxy-[1]benzopyrano[3,4-b]pyrrol-4(3H)-one | 1519002-23-3

• 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-[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)-7-propan-2-yloxy-3H-chromeno[3,4-b]pyrrol-4-one
• CAS: 1519002-23-3
• 化学式: C₃₅H₃₉NO₈
• 分子量: 601.697
• InChiKey: IYVPDBZIPJYPSR-UHFFFAOYSA-N

物化性质

• 沸点：
  724.3±60.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  97.5
• 氢给体数：
  1
• 氢受体数：
  8

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-[1]benzopyrano[3,4-b]pyrrol-4(3H)-one 在 三氟甲磺酸三甲基硅酯 、 caesium carbonate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.25h， 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：

  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 、 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 55.5h， 生成 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

文献信息

• Synthesis of Lamellarins via Regioselective Assembly of 1,2-Diarylated [1]Benzopyrano[3,4-b]pyrrol-4(3H)-one Core
  作者：Tsutomu Fukuda、Takatoshi Katae、Issei Harada、Masatomo Iwao

  DOI：10.3987/com-16-s(s)63

  日期：——

  A modular synthesis of lamellarins has been developed. The key reactions in this synthesis are the assembly of 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-ones from a preexisting [1]benzopyrano[3,4-b]pyrrol4(3H)-one core and the appropriate arylboronic acids. The obtained 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-ones could be easily converted into the corresponding lamellarin derivatives

  已经开发了层状蛋白的模块化合成。该合成中的关键反应是由预先存在的[1]苯并吡喃[3,4-b]吡咯4( 3H)-一个核心和适当的芳基硼酸。得到的1,2-二芳基[1]苯并吡喃[3,4-b]pyrrol-4(3H)-ones可以通过吡咯氮和C2芳环之间的分子内环化很容易地转化为相应的层状结构衍生物。引言 层层素是一种多环吡咯生物碱，具有独特的 14-苯基-6H-[1]苯并吡喃[4́,3́:4,5]吡咯并[2,1-a]异喹啉-6-环系统。在极少数情况下（层状蛋白 O、P、Q 和 R），这些化合物具有简单的非稠合 3,4-diarylpyrrole-2-carboxylate 结构。自从第一次从海洋前支软体动物 Lamellaria sp. 中分离出层状蛋白 A-D。1985 年，从被囊类动物、海绵类和前枝类动物中分离出 50 多种层状蛋白。这些层状蛋白表现出广泛的有用生物活性：针对几种癌细胞系的有效抗增殖活性、多药耐药性
• 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.