2,2,5,5-tetramethyl-3,3a,4,5-tetrahydro-2H-pyrano<4,3,2-de>-1-benzopyran-8-ol | 147750-08-1

• 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: 2,2,5,5-tetramethyl-3,3a,4,5-tetrahydro-2H-pyrano<4,3,2-de>-1-benzopyran-8-ol
• 英文别名: 3,3,7,7-Tetramethyl-2,8-dioxatricyclo[7.3.1.05,13]trideca-1(12),9(13),10-trien-11-ol
• CAS: 147750-08-1
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: UYYOQCKKDVEJOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,5,5-tetramethyl-3,3a,4,5-tetrahydro-2H-pyrano<4,3,2-de>-1-benzopyran-8-ol 在 四氯化钛 、 sodium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 11-Methoxy-3,3,7,7-tetramethyl-2,8-dioxatricyclo[7.3.1.05,13]trideca-1(12),9(13),10-triene-10,12-dicarbaldehyde
  参考文献：
  名称：

  Aukrust, Inger Reidun; Bakstad, Einar; Skatteboel, Lars, Acta Chemica Scandinavica, 1993, vol. 47, # 3, p. 314 - 317

  摘要：

  DOI：
• 作为产物：
  描述：

  5,7-二羟基-2,2-二甲基-2,3-二氢-4H-苯并吡喃-4-酮 在 盐酸 、 锌 作用下， 反应 1.33h， 生成 2,2,5,5-tetramethyl-3,3a,4,5-tetrahydro-2H-pyrano<4,3,2-de>-1-benzopyran-8-ol
  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.
• Aukrust, Inger Reidun; Bakstad, Einar; Skatteboel, Lars, Acta Chemica Scandinavica, 1993, vol. 47, # 3, p. 314 - 317
  作者：Aukrust, Inger Reidun、Bakstad, Einar、Skatteboel, Lars

  DOI：——

  日期：——