2,2,4-三甲基-3H-苯并[g][1]苯并呋喃-5-醇 | 151799-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 中文名称: 2,2,4-三甲基-3H-苯并[g][1]苯并呋喃-5-醇
• 英文名称: Naphtho[1,2-b]furan-5-ol, 2,3-dihydro-2,2,4-trimethyl-
• 英文别名: 2,2,4-trimethyl-3H-benzo[g][1]benzofuran-5-ol
• CAS: 151799-19-8
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: XJBJQGZQJNMGCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  398.8±41.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,4-三甲基-3H-苯并[g][1]苯并呋喃-5-醇 在 sodium hydroxide 、 air 、 potassium hexacyanoferrate(III) 作用下， 以 甲苯 为溶剂， 反应 169.0h， 生成 1,2-Ethylene-2,2'-bis[3-(2-hydroxy-2-methylpropyl)-1,4-naphthoquinone]
  参考文献：
  名称：

  Schaedel, Uta; Habicher, Wolf D., Synthesis, 1998, # 3, p. 293 - 296

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-Hydroxy-2-methylpropyl)-3-methyl-1,4-naphthoquinone 在 溶剂黄146 、 锌 作用下， 反应 2.0h， 以96%的产率得到2,2,4-三甲基-3H-苯并[g][1]苯并呋喃-5-醇
  参考文献：
  名称：

  Schaedel, Uta; Habicher, Wolf D., Synthesis, 1998, # 3, p. 293 - 296

  摘要：

  DOI：

文献信息

• Chain-breaking phenolic antioxidants: steric and electronic effects in polyalkylchromanols, tocopherol analogs, hydroquinones, and superior antioxidants of the polyalkylbenzochromanol and naphthofuran class
  作者：L. R. C. Barclay、M. R. Vinqvist、K. Mukai、S. Itoh、H. Morimoto

  DOI：10.1021/jo00078a020

  日期：1993.12

  Antioxidant activities of four classes of phenols were measured by the inhibition of thermally initiated autoxidation of styrene at 30-degrees-C. Class I, 6-hydroxypolyalkylchromans (model compounds) showed the same inhibition rate constants (k(inh) as their alpha-tocopherol analogs, in the range 1.5 X 10(6) M-1 s-1 to 3.8 x 10(6) M-1 s-1 for two methyl or ethyl groups ortho to the phenolic hydroxyl group. Bulky ortho groups reduce the k(inh), two isopropyl groups by 3-fold and 5-isopropyl-6-tert-butyl by 5-fold, compared to that of alpha-tocopherol, due to steric hindrance to the approach of peroxyl radicals. Class II, the a-naphthol derivatives, 6-hydroxy-2,5-dimethyl-2-phytyl-7,8-benzochroman (9a) and the corresponding chromene (9b), exhibit higher k(inh) values, 4 times that of alpha-tocopherol. A new synthetic antioxidant, 2,3-dihydro-5-hydroxy-2,2,4-trimethylnaphtho[1,2-b]furan, exhibits k(inh) = 2.87 x 10(7) M-1 s-1, 10 times that of a-tocopherol or any model compound, and is the most active phenolic antioxidant known. Class III, hydroquinones including 2,3,6-trimethylhydroquinone and the alpha-, beta-, and gamma-tocopherylhydroquinones, are 2 to 4 times less active as antioxidants than a-tocopherol, and class IV, the ubiquinones, are 8-10 times less active than a-tocopherol. The stoichiometric factors, n, for peroxyl radical trapping are 1.5-2.0 for phenols of classes I and II, 1.0-1.9 for ubiquinones but less than 0.5 for hydroquinones of class III due to ''wasting'' oxidation reactions of the latter. Antioxidant activities in solution are interpreted in terms of steric hindrance, retarding hydrogen transfer to peroxyl radicals, and electronic effects which increase k(inh) by stabilization of the ArO. radicals. Results in styrene solution are in contrast with other data in aqueous lipid membranes where H-bonding by water on the antioxidants is a significant effect on k(inh).
• Schaedel, Uta; Habicher, Wolf D., Synthesis, 1998, # 3, p. 293 - 296
  作者：Schaedel, Uta、Habicher, Wolf D.

  DOI：——

  日期：——