(2R,2'R,4'S)-5,7-dihydroxy-3',3'-dimethyl-2',4'-methanospiro-4-one | 175775-64-1

• 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: (2R,2'R,4'S)-5,7-dihydroxy-3',3'-dimethyl-2',4'-methanospiro-4-one
• 英文别名: (2R,2'R,4'S)-5,7-dihydroxy-3',3'-dimethyl-2',4'-methanospiro(chroman-2,1'-cyclohexan)-4-one；(1'R,2R,5'S)-5,7-dihydroxy-6',6'-dimethylspiro[3H-chromene-2,2'-bicyclo[3.1.1]heptane]-4-one
• CAS: 175775-64-1
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: CJMACRKZAKPMJP-PIAMENMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,2'R,4'S)-5,7-dihydroxy-3',3'-dimethyl-2',4'-methanospiro-4-one 在 palladium on activated charcoal 五氯化磷 、 硫酸 、 氢气 、 锌 、 三氯氧磷 作用下， 反应 8.33h， 生成
  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：

  (1R,5S)-6,6-dimethylbicyclo<3.1.1>heptan-2-ylideneacetaldehyde 在 sodium hydroxide 、 草酰氯 、 silver nitrate 、 zinc(II) chloride 作用下， 以 乙醚 、 乙醇 、 水 、 苯 为溶剂， 反应 27.0h， 生成 (2R,2'R,4'S)-5,7-dihydroxy-3',3'-dimethyl-2',4'-methanospiro-4-one
  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

文献信息

• The Synthesis of (-)-Robustadial A and Some Analogues.
  作者：Inger Reidun Aukrust、Lars Skattebøl、Otto Dahl、Georg Hvistendahl、Markku Leskelä、Mika Polamo、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0132

  日期：——

  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.