5,5',6,6',7,7'-hexamethoxy-4,8'-dimethyl-3H-spiro[isobenzofuran-1,3'-isochroman]-4'-one | 1616693-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,5',6,6',7,7'-hexamethoxy-4,8'-dimethyl-3H-spiro[isobenzofuran-1,3'-isochroman]-4'-one
• 英文别名: 4,5,5',6,6',7'-hexamethoxy-7,8'-dimethylspiro[1H-2-benzofuran-3,3'-1H-isochromene]-4'-one
• CAS: 1616693-43-6
• 化学式: C₂₄H₂₈O₉
• 分子量: 460.481
• InChiKey: JJQRYVJZLKYSFP-UHFFFAOYSA-N

物化性质

• 沸点：
  657.7±55.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5,5',6,6',7,7'-hexamethoxy-4,8'-dimethyl-3H-spiro[isobenzofuran-1,3'-isochroman]-4'-one 在 chiral-phase (CHIRALPAK ADH) HPLC column 作用下， 以 正己烷 、 异丙醇 为溶剂， 以9.1 mg的产率得到(3S)-4,5,5',6,6',7'-hexamethoxy-7,8'-dimethylspiro[1H-2-benzofuran-3,3'-1H-isochromene]-4'-one
  参考文献：
  名称：

  Eleganketal A, a Highly Oxygenated Dibenzospiroketal from the Marine-Derived Fungus Spicaria elegans KLA03

  摘要：

  Eleganketal A (1), a naturally occurring aromatic polyketide possessing a rare highly oxygenated spiro[isobenzofuran-1,3'-isochroman] ring system, was isolated from the fungus Spicaria elegans KLA03 by culturing it in a modified mannitol-based medium. The structure of 1 including the absolute configuration was determined by combining spectroscopic analysis, synthesis of the racemic permethylated analogue, chiral-phase HPLC separation, and TDDFT-ECD analysis.

  DOI：

  10.1021/np500458a
• 作为产物：
  描述：

  3,4,5-三甲氧基-2-溴苯甲醛 在 ruthenium trichloride 、 sodium tetrahydroborate 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 potassium metaperiodate 、 碘 、 silver trifluoroacetate 、 三溴化磷 、 对甲苯磺酸 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 氯仿 、 水 、 甲苯 、 乙腈 为溶剂， 反应 69.5h， 生成 5,5',6,6',7,7'-hexamethoxy-4,8'-dimethyl-3H-spiro[isobenzofuran-1,3'-isochroman]-4'-one
  参考文献：
  名称：

  Eleganketal A, a Highly Oxygenated Dibenzospiroketal from the Marine-Derived Fungus Spicaria elegans KLA03

  摘要：

  Eleganketal A (1), a naturally occurring aromatic polyketide possessing a rare highly oxygenated spiro[isobenzofuran-1,3'-isochroman] ring system, was isolated from the fungus Spicaria elegans KLA03 by culturing it in a modified mannitol-based medium. The structure of 1 including the absolute configuration was determined by combining spectroscopic analysis, synthesis of the racemic permethylated analogue, chiral-phase HPLC separation, and TDDFT-ECD analysis.

  DOI：

  10.1021/np500458a

文献信息

• Palladium-catalyzed intermolecular tandem cyclization reaction: a highly regioselective synthesis of functionalized 3H-spiro[isobenzofuran-1,3′-isochroman] scaffolds
  作者：Liang Wang、Xuehu Li、Hua Tao、Xiang Zhou、Xihong Lu、Wenyue Du、Tingting Jiang、Zhijun Xin、Jianping Liang

  DOI：10.1039/c6ob02802k

  日期：——

  functionalized 3H-spiro[isobenzofuran-1,3′-isochroman] scaffolds using a novel palladium-catalyzed tandem cyclization reaction is explored. During the reaction process, C–O, C–C and C–O bonds are sequentially formed in one pot via decarboxylative allenylpalladium formation, nucleophilic attack, arylpalladium addition and intramolecular nucleophilic attack.

  探索了使用新型钯催化串联环化反应的功能性3 H-螺[异苯并呋喃-1,3'-异色满]支架的高度区域选择性合成。在反应过程中，通过脱羧化烯基钯的形成，亲核攻击，芳基钯加成和分子内亲核攻击，在一个罐中依次形成C–O ，CC和C–O键。
• Eleganketal A, a Highly Oxygenated Dibenzospiroketal from the Marine-Derived Fungus <i>Spicaria elegans</i> KLA03
  作者：Yepeng Luan、Hongjuan Wei、Zhenpei Zhang、Qian Che、Yankai Liu、Tianjiao Zhu、Attila Mándi、Tibor Kurtán、Qianqun Gu、Dehai Li

  DOI：10.1021/np500458a

  日期：2014.7.25

  Eleganketal A (1), a naturally occurring aromatic polyketide possessing a rare highly oxygenated spiro[isobenzofuran-1,3'-isochroman] ring system, was isolated from the fungus Spicaria elegans KLA03 by culturing it in a modified mannitol-based medium. The structure of 1 including the absolute configuration was determined by combining spectroscopic analysis, synthesis of the racemic permethylated analogue, chiral-phase HPLC separation, and TDDFT-ECD analysis.