(+/-)-(3aR,7S,7aS)-7-(2,5-dimethoxyphenyl)perhydroisoindole-1,3,5-trione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (+/-)-(3aR,7S,7aS)-7-(2,5-dimethoxyphenyl)perhydroisoindole-1,3,5-trione
• 英文别名: (3aR,7S,7aS)-7-(2,5-dimethoxyphenyl)-4,6,7,7a-tetrahydro-3aH-isoindole-1,3,5-trione
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: IUCCRNTVOVRMRJ-BZPMIXESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-4-(2,5-dimethoxyphenyl)but-3-en-2-one 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 (+/-)-(3aR,7S,7aS)-7-(2,5-dimethoxyphenyl)perhydroisoindole-1,3,5-trione
  参考文献：
  名称：

  Open Analogues of Arcyriaflavin A. Synthesis through Diels−Alder Reaction between Maleimides and 1-Aryl-3-tert-butyldimethylsiloxy-1,3-butadienes

  摘要：

  The preparation of a range of open analogues of arcyriaflavin A is described. The synthetic approach is based on the use of perhydroisoindole-1,3,5-triones as key intermediates, which were obtained via Diels-Alder methodology using 1-aryl-3-siloxy-1,3-butadienes as starting materials. Fischer indolization and aromatization processes afforded different methoxy-substituted arylpyrrolocarbazoles. The stereochemistry and conformation of the Diels-Alder products and the regiochemistry of the indolization reactions are supported by NMR and molecular modeling studies.

  DOI：

  10.1021/jo991815x

文献信息

• Open Analogues of Arcyriaflavin A. Synthesis through Diels−Alder Reaction between Maleimides and 1-Aryl-3-<i>tert</i>-butyldimethylsiloxy-1,3-butadienes
  作者：Marta Adeva、Heidi Sahagún、Esther Caballero、Rafael Peláez-Lamamié de Clairac、Manuel Medarde、Fernando Tomé

  DOI：10.1021/jo991815x

  日期：2000.6.1

  The preparation of a range of open analogues of arcyriaflavin A is described. The synthetic approach is based on the use of perhydroisoindole-1,3,5-triones as key intermediates, which were obtained via Diels-Alder methodology using 1-aryl-3-siloxy-1,3-butadienes as starting materials. Fischer indolization and aromatization processes afforded different methoxy-substituted arylpyrrolocarbazoles. The stereochemistry and conformation of the Diels-Alder products and the regiochemistry of the indolization reactions are supported by NMR and molecular modeling studies.