5,7-dihydroxyspiro-4-one | 135110-70-2

• 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-dihydroxyspiro-4-one
• 英文别名: 5,7-dihydroxyspiro(chroman-2,1'-cyclopentan)-4-one；5,7-Dihydroxyspiro[2H-1-benzopyran-2,1a(2)-cyclopentan]-4(3H)-one；5,7-dihydroxyspiro[3H-chromene-2,1'-cyclopentane]-4-one
• CAS: 135110-70-2
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: MZBSHYSBLBXXDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  5,7-dihydroxyspiro-4-one 在 palladium on activated charcoal 盐酸 、 氢气 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.33h， 生成 5',5'-dimethyl-3',3a',4',5'-tetrahydrospiropyrano<4,3,2-de><1>benzopyran>-8'-ol
  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：

  间苯三酚 、 2-环戊基乙酸 在 三氯化铝 、 三氯氧磷 作用下， 反应 6.0h， 以81%的产率得到5,7-dihydroxyspiro-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

• US4185112A
  申请人：——

  公开号：US4185112A

  公开（公告）日：1980-01-22
• US4415741A
  申请人：——

  公开号：US4415741A

  公开（公告）日：1983-11-15
• US4479007A
  申请人：——

  公开号：US4479007A

  公开（公告）日：1984-10-23
• 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：——