5,7-dihydroxy-4-isobutylspiro | 175611-72-0

• 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: 5,7-dihydroxy-4-isobutylspiro
• 英文别名: 5,7-dihydroxy-4-isobutylspiro(chroman-2,1'-cyclopentane)；4-(2-methylpropyl)spiro[3,4-dihydrochromene-2,1'-cyclopentane]-5,7-diol
• CAS: 175611-72-0
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: LCUBWUBZKHMKOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,1-二氯甲醚 、 5,7-dihydroxy-4-isobutylspiro 在 四氯化钛 作用下， 以 氯仿 为溶剂， 反应 7.0h， 以43%的产率得到6,8-diformyl-5,7-dihydroxy-4-isobutylspiro
  参考文献：
  名称：

  The Synthesis of (-)-Robustadial A and Some Analogues.

  摘要：

  The naturally occurring chroman derivative, robustadial A, and several analogues have been prepared by a four-step synthesis starting from phloroglucinol. The synthetic scheme involves as the first step a Friedel-Crafts condensation of an alpha,beta-unsaturated acid derivative with phloroglucinol to the corresponding chromanone. The isobutyl group at the 4-position was introduced with methallylzine bromide followed by hydrogenation, carried out as a one-pot reaction. Finally, both aldehyde functions were attached using dichloromethyl methyl ether and titanium tetrachloride. Optically pure 6,6-dimethylbicyclo[3.1.1]heptan-2-ylidene-acetic acid, needed for the synthesis of robustadial, was prepared from (-)-nopol by two consecutive oxidations in 77% overall yield.

  DOI：

  10.3891/acta.chem.scand.50-0132
• 作为产物：
  描述：

  环戊-1-烯-1-乙酸 在 palladium on activated charcoal 三氯化铝 、 硫酸 、 氢气 、 锌 、 三氯氧磷 作用下， 反应 7.33h， 生成 5,7-dihydroxy-4-isobutylspiro
  参考文献：
  名称：

  The Synthesis of (-)-Robustadial A and Some Analogues.

  摘要：

  The naturally occurring chroman derivative, robustadial A, and several analogues have been prepared by a four-step synthesis starting from phloroglucinol. The synthetic scheme involves as the first step a Friedel-Crafts condensation of an alpha,beta-unsaturated acid derivative with phloroglucinol to the corresponding chromanone. The isobutyl group at the 4-position was introduced with methallylzine bromide followed by hydrogenation, carried out as a one-pot reaction. Finally, both aldehyde functions were attached using dichloromethyl methyl ether and titanium tetrachloride. Optically pure 6,6-dimethylbicyclo[3.1.1]heptan-2-ylidene-acetic acid, needed for the synthesis of robustadial, was prepared from (-)-nopol by two consecutive oxidations in 77% overall yield.

  DOI：

  10.3891/acta.chem.scand.50-0132