4,5-dihydroxy-benzo<2H>dihydropyran | 143536-29-2

• 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: 4,5-dihydroxy-benzo<2H>dihydropyran
• 英文别名: Isochroman-4,5-diol；3,4-dihydro-1H-isochromene-4,5-diol
• CAS: 143536-29-2
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: GRLXVSRSTWJKSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-羟基苯甲醇 在 palladium on activated charcoal sodium hydroxide 、 硫酸 、 氢气 、 四丁基硫酸氢铵 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 27.75h， 生成 4,5-dihydroxy-benzo<2H>dihydropyran
  参考文献：
  名称：

  Regioselective synthesis of 1,8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl)alkanoates

  摘要：

  A series of 4-(3-hydroxyphenyl)butanoates 3 has been prepared and transformed into 1,8-dihydroxytetralins of general formula 2 by treatment with 2 equivalents of DIBALH followed by quenching with aqueous NH4Cl. A possible mechanism for this novel totally regioselective intramolecular hydroxyalkylation is suggested and the factors affecting the stability of 1,8-dihydroxytetralins 2 are also discussed.

  DOI：

  10.1016/s0040-4020(01)89307-8

文献信息

• Tandem reduction / intramolecular hydroxyalkylation of (3-hydroxyphenyl)alkanoates: a new regioselective approach to 1,8-dihydroxytetralins
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano、Renata Riva、Sergio Thea

  DOI：10.1016/s0040-4039(00)74819-2

  日期：1992.6

  4-(3-hydroxyphenyl)-butanoates 4, on treatment with DIBALH, followed by hydrolytic work-up, undergo a novel completely regioselective intramolecular hydroxyalkylation reaction to give 1,8-dihydroxytetralins. The yield of the reaction depends heavily on the structure of starting material, best results being achieved with 3,3-disubstituted butanoates.
• Regioselective synthesis of 1,8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl)alkanoates
  作者：Giuseppe Guanti、Luca Banfi、Renata Riva

  DOI：10.1016/s0040-4020(01)89307-8

  日期：1994.1

  A series of 4-(3-hydroxyphenyl)butanoates 3 has been prepared and transformed into 1,8-dihydroxytetralins of general formula 2 by treatment with 2 equivalents of DIBALH followed by quenching with aqueous NH4Cl. A possible mechanism for this novel totally regioselective intramolecular hydroxyalkylation is suggested and the factors affecting the stability of 1,8-dihydroxytetralins 2 are also discussed.