O-methylruprechstyril | 1161720-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: O-methylruprechstyril
• 英文别名: 6,8-dimethoxy-3-pentyl-2H-isoquinolin-1-one
• CAS: 1161720-28-0
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: VWTHINMCQYBBJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-methylruprechstyril 在 aluminum (III) chloride 作用下， 以 乙硫醇 为溶剂， 反应 1.0h， 以81%的产率得到6,8-dihydroxy-3-pentyl-2H-isoquinolin-1-one
  参考文献：
  名称：

  An efficient total synthesis of ruprechstyril fromRuprechtia tangarana

  摘要：

  A short total synthesis of natural isocarbostyril ruprechstyril (3-n-pentyl-6-methoxy-8-hydroxy-1(2H)-isoquinolinone) isolated from Ruprechtia tangarana is reported. 6,8-Dimethoxy-3-pentylisocoumarin obtained by condensation of 3,5-dimethoxyhomophthalic anhydride with hexanoyl chloride was smoothly converted to O-methylruprechstyril by refluxing with methanamide. Regioselective demethylation of the latter using anhydrous aluminium chloride in dichloromethane furnished the ruprechstyril. Complete demethylation to give (6-desmethoxyruprechstyril) was achieved using same reagent in ethanethiol.

  DOI：

  10.1080/14786419.2012.715292
• 作为产物：
  描述：

  6,8-dimethoxy-1H-2-benzopyran-1,3(4H)-dione 在 四甲基胍 作用下， 以 乙腈 为溶剂， 反应 4.66h， 生成 O-methylruprechstyril
  参考文献：
  名称：

  An efficient total synthesis of ruprechstyril fromRuprechtia tangarana

  摘要：

  A short total synthesis of natural isocarbostyril ruprechstyril (3-n-pentyl-6-methoxy-8-hydroxy-1(2H)-isoquinolinone) isolated from Ruprechtia tangarana is reported. 6,8-Dimethoxy-3-pentylisocoumarin obtained by condensation of 3,5-dimethoxyhomophthalic anhydride with hexanoyl chloride was smoothly converted to O-methylruprechstyril by refluxing with methanamide. Regioselective demethylation of the latter using anhydrous aluminium chloride in dichloromethane furnished the ruprechstyril. Complete demethylation to give (6-desmethoxyruprechstyril) was achieved using same reagent in ethanethiol.

  DOI：

  10.1080/14786419.2012.715292

文献信息

• Synthetic Studies on Natural Isocoumarins and Isocarbostyril Derivatives Having an Alkyl Substituent at the 3-Position: Total Synthesis of Scoparines A and B, and Ruprechstyril
  作者：Toshio Honda、Marcellino Rudyanto、Koichi Kobayashi

  DOI：10.3987/com-08-s(d)40

  日期：——

  Two isocoumarins, scoparines A and B, having n-propyl group at the 3-position, and a new isocarbostynl, ruprechstynl, beanng n-pentyl substituent at the 3-position were synthesized via Sonogashira coupling of the corresponding aromatic halides and alkynes, followed by regioselective 6-endo-dig cyclization.

  通过相应的芳族卤化物和炔烃的 Sonogashira 偶联，合成了两种异香豆素，东芝碱 A 和 B，在 3 位具有正丙基，并在 3 位具有新的异卡波炔基、ruprechsynl、beanng 正戊基取代基，然后通过区域选择性 6-endo-dig 环化。
• An efficient total synthesis of ruprechstyril from<i>Ruprechtia tangarana</i>
  作者：Aamer Saeed

  DOI：10.1080/14786419.2012.715292

  日期：2013.7

  A short total synthesis of natural isocarbostyril ruprechstyril (3-n-pentyl-6-methoxy-8-hydroxy-1(2H)-isoquinolinone) isolated from Ruprechtia tangarana is reported. 6,8-Dimethoxy-3-pentylisocoumarin obtained by condensation of 3,5-dimethoxyhomophthalic anhydride with hexanoyl chloride was smoothly converted to O-methylruprechstyril by refluxing with methanamide. Regioselective demethylation of the latter using anhydrous aluminium chloride in dichloromethane furnished the ruprechstyril. Complete demethylation to give (6-desmethoxyruprechstyril) was achieved using same reagent in ethanethiol.