(2R,4R,2'R,4'S)-5,7-dihydroxy-4-isobutyl-3,3'-dimethyl-2',4'-methanospiro | 175611-70-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,4R,2'R,4'S)-5,7-dihydroxy-4-isobutyl-3,3'-dimethyl-2',4'-methanospiro
• 英文别名: (2R,4R,2'R,4'S)-5,7-dihydroxy-4-isobutyl-3,3'-dimethyl-2',4'-methanospiro(chroman-2,1'-cyclohexane)；(1'R,2R,4R,5'S)-6',6'-dimethyl-4-(2-methylpropyl)spiro[3,4-dihydrochromene-2,2'-bicyclo[3.1.1]heptane]-5,7-diol
• CAS: 175611-70-8
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: DJZJZSCWEWHBGZ-PKEAVRCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-二氯甲醚 、 (2R,4R,2'R,4'S)-5,7-dihydroxy-4-isobutyl-3,3'-dimethyl-2',4'-methanospiro 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以15%的产率得到4-(4'-{[(3-羟基-3,4-二氢-2H-1,5-苯并二氧杂卓-3-基)甲基]硫基}-4-联苯基)-2,4-二氧代丁酸
  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,2E)-6,6-dimethylbicyclo<3.1.1>heptan-2-ylideneacetyl chloride 在 palladium on activated charcoal 硫酸 、 氢气 、 zinc(II) chloride 、 锌 作用下， 以 乙醚 为溶剂， 反应 3.33h， 生成 (2R,4R,2'R,4'S)-5,7-dihydroxy-4-isobutyl-3,3'-dimethyl-2',4'-methanospiro
  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.