2,3-dihydro-2,2,6,7-tetramethylbenzofuran-5-ol | 26172-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,3-dihydro-2,2,6,7-tetramethylbenzofuran-5-ol
• 英文别名: 2,2,6,7-Tetramethyl-2,3-dihydrobenzofuran-5-ol；2,2,6,7-tetramethyl-3H-1-benzofuran-5-ol
• CAS: 26172-18-9
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: OVEJSFXCEFGPCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2,3-dihydro-2,2,6,7-tetramethylbenzofuran-5-ol 在 水 、 tert-butylammonium hexafluorophosphate(V) 作用下， 以 乙腈 为溶剂， 生成 5-(2-Hydroxy-2-methyl-propyl)-2,3-dimethyl-[1,4]benzoquinone
  参考文献：
  名称：

  结构类似于维生素E的酚氧化过程中产生的苯氧鎓阳离子的红外和UV-vis光谱

  摘要：

  几种具有类似于维生素E的结构的酚被氧化，产生的中间物种通过原位红外和紫外可见光谱进行表征。通过用2摩尔当量化学氧化苯酚来进行傅里叶变换红外（FTIR）测量。NO的+的SbF 6 -的CH 3 CN和记录1900和1300厘米光谱-1与衰减全反射利用（ATR）探针的纤维导管和金刚石复合传感器。形成长寿命苯氧鎓阳离子的化合物在1665（±15）cm -1处显示出两种红外吸收，在1600（±10）cm -1处显示出一种红外吸收。与羰基，对称环拉伸和不对称环拉伸模式相关。对苯醌是酚氧化的长期产物之一，并且在1650（±10）cm -1处显示出溶液相的IR吸光度。在苯酚氧化过程中进行的原位电化学UV-vis实验导致检测到条带，这是由于在295（±5）和440（±15）nm处的苯氧鎓阳离子以及在260（±10）nm处的对醌）nm。底物的浓度和溶剂的水含量对在氧化反应过程中产生的中间体和产物的收率有重大影响。

  DOI：

  10.1016/j.electacta.2010.07.096
• 作为产物：
  描述：

  2,3-dimethyl-5-<(2-methyl)-2-propenyl>hydroquinone 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 以91%的产率得到2,3-dihydro-2,2,6,7-tetramethylbenzofuran-5-ol
  参考文献：
  名称：

  A rapid screening test to determine the antioxidant potencies of natural and synthetic antioxidants

  摘要：

  This paper presents a simple and convenient method for measuring antioxidant efficiencies in a model system consisting of micelles of sodium dodecyl sulfate (SDS) with added linoleic acid. The analytical method involves following the development of absorption at 234 nm due to the conjugated diene hydroperoxide of linoleic acid; 2,2'-azobis(2-amidinopropane) dihydrochloride (ABAP) is used as the initiator. The antioxidant efficiency of an antioxidant is defined as AE = k(inh)/k(p), where k(inh) is the rate constant for reaction of the peroxyl radical from linoleic acid with the antioxidant (eq 7 in the text) and k(p) is the propagation rate constant for autoxidation of linoleic acid (eq 5). The relative antioxidant efficiency (RAE) is defined as the AE of the test compound divided by that for alpha-tocopherol; thus, RAE values are equal to k(inh)/k(inh,alpha-tocopherol). Since the absolute value of the rate constant for reaction of alpha-tocopherol with peroxyl radicals is known in micellar systems, the absolute value of k(inh) for a given antioxidant can be calculated if required. To establish the reliability of the method we report the AE of 17 synthetic and naturally occurring antioxidants and compare values obtained by this method to others in the literature. For neutral antioxidants, the same AE values are obtained in both negatively-charged micelles of SDS and positively-charged micelles of hexadecyl trimethylammonium bromide (HDTBr). The relative antioxidant efficiencies are reported for more than 40 synthetic compounds that are potential antioxidants or anti-inflammatory compounds; most of these compounds are tocopherol, ascorbate, or 2-hydroxytetronic acid analogues. Although the charge type of the micelle has no effect on the RAE of neutral antioxidants, micelles of different charge types do have an effect on the RAE value of charged antioxidants such as ascorbic acid, other 2-hydroxytetronic acids, and Trolox C. In 0.10 M SDS micelles, ascorbic acid and alpha-tocopherol are shown to have an additive effect, not a synergistic effect, as antioxidants.

  DOI：

  10.1021/jo00065a013

文献信息

• The directing effect of annelated rings in aromatic systems—II
  作者：J. Lars、G. Nilsson、H. Selander、H. Sievertsson、I. Skånberg

  DOI：10.1016/s0040-4020(01)97886-x

  日期：——

  2-dimethyl-5-benzofuranol gave a spiroketal trimer 10 by CC and CO coupling via the 6-position of the molecule. This indicates a directing effect on the oxidative coupling by the annelated 5-membered heterocyclic ring which is in accord with the predictions based on the Mills-Nixon effect. Similar oxidation of 2,3-dihydro-2,2,4,7-tetramethyl-5-benzofuranol and of 2,3-dihydro-2,2,6,7-tetramethyl-5-benzofuranol

  合成了与β-，γ-生育酚和母育酚有关的2,3二氢-5-苯并呋喃醇，并研究了其与碱性铁氰化物的氧化作用。2,3-二氢-2,2-二甲基-5-苯并呋喃醇的氧化通过分子的6位进行CC和CO偶合，得到了螺酮三聚体10。这表明退火的五元杂环对氧化偶联的指导作用，这与基于Mills-Nixon效应的预测相符。2,3-二氢-2,2,4,7-四甲基-5-苯并呋喃醇的相似氧化反应和2,3-二氢-2,2,6,7-四甲基-5-苯并呋喃醇的氧化反应（β-和γ的类似物-生育酚）分别通过涉及杂环开环的反应得到羟基醌11和12。
• Al-Khayat, Isam; Dean, Francis M.; France, Steven N., Journal of the Chemical Society. Perkin transactions I, 1985, p. 1301 - 1310
  作者：Al-Khayat, Isam、Dean, Francis M.、France, Steven N.、Matkin, David A.、Orabi, Mohamed O. A.、et al.

  DOI：——

  日期：——
• Dean, Frabcis M.; Orabi, Mohamed O. A., Journal of the Chemical Society. Perkin transactions I, 1982, # 11, p. 2617 - 2624
  作者：Dean, Frabcis M.、Orabi, Mohamed O. A.

  DOI：——

  日期：——
• Infrared and UV–vis spectra of phenoxonium cations produced during the oxidation of phenols with structures similar to vitamin E
  作者：Shanshan Chen、Hong Mei Peng、Richard D. Webster

  DOI：10.1016/j.electacta.2010.07.096

  日期：2010.12

  Several phenols with structures similar to vitamin E were oxidised and the intermediate species produced were characterised by in situ infrared and UV–vis spectroscopies. The Fourier transform infrared (FTIR) measurements were performed by chemically oxidising the phenols with 2 mol equiv. of NO+SbF6− in CH3CN and recording the spectra between 1900 and 1300 cm−1 with an attenuated total reflectance

  几种具有类似于维生素E的结构的酚被氧化，产生的中间物种通过原位红外和紫外可见光谱进行表征。通过用2摩尔当量化学氧化苯酚来进行傅里叶变换红外（FTIR）测量。NO的+的SbF 6 -的CH 3 CN和记录1900和1300厘米光谱-1与衰减全反射利用（ATR）探针的纤维导管和金刚石复合传感器。形成长寿命苯氧鎓阳离子的化合物在1665（±15）cm -1处显示出两种红外吸收，在1600（±10）cm -1处显示出一种红外吸收。与羰基，对称环拉伸和不对称环拉伸模式相关。对苯醌是酚氧化的长期产物之一，并且在1650（±10）cm -1处显示出溶液相的IR吸光度。在苯酚氧化过程中进行的原位电化学UV-vis实验导致检测到条带，这是由于在295（±5）和440（±15）nm处的苯氧鎓阳离子以及在260（±10）nm处的对醌）nm。底物的浓度和溶剂的水含量对在氧化反应过程中产生的中间体和产物的收率有重大影响。
• A rapid screening test to determine the antioxidant potencies of natural and synthetic antioxidants
  作者：William A. Pryor、Joseph A. Cornicelli、Larry J. Devall、Bradley Tait、B. K. Trivedi、D. T. Witiak、Mingdan Wu

  DOI：10.1021/jo00065a013

  日期：1993.6

  This paper presents a simple and convenient method for measuring antioxidant efficiencies in a model system consisting of micelles of sodium dodecyl sulfate (SDS) with added linoleic acid. The analytical method involves following the development of absorption at 234 nm due to the conjugated diene hydroperoxide of linoleic acid; 2,2'-azobis(2-amidinopropane) dihydrochloride (ABAP) is used as the initiator. The antioxidant efficiency of an antioxidant is defined as AE = k(inh)/k(p), where k(inh) is the rate constant for reaction of the peroxyl radical from linoleic acid with the antioxidant (eq 7 in the text) and k(p) is the propagation rate constant for autoxidation of linoleic acid (eq 5). The relative antioxidant efficiency (RAE) is defined as the AE of the test compound divided by that for alpha-tocopherol; thus, RAE values are equal to k(inh)/k(inh,alpha-tocopherol). Since the absolute value of the rate constant for reaction of alpha-tocopherol with peroxyl radicals is known in micellar systems, the absolute value of k(inh) for a given antioxidant can be calculated if required. To establish the reliability of the method we report the AE of 17 synthetic and naturally occurring antioxidants and compare values obtained by this method to others in the literature. For neutral antioxidants, the same AE values are obtained in both negatively-charged micelles of SDS and positively-charged micelles of hexadecyl trimethylammonium bromide (HDTBr). The relative antioxidant efficiencies are reported for more than 40 synthetic compounds that are potential antioxidants or anti-inflammatory compounds; most of these compounds are tocopherol, ascorbate, or 2-hydroxytetronic acid analogues. Although the charge type of the micelle has no effect on the RAE of neutral antioxidants, micelles of different charge types do have an effect on the RAE value of charged antioxidants such as ascorbic acid, other 2-hydroxytetronic acids, and Trolox C. In 0.10 M SDS micelles, ascorbic acid and alpha-tocopherol are shown to have an additive effect, not a synergistic effect, as antioxidants.